Indazole-aminoacetonitrile derivatives having special pesticidal activity

ABSTRACT

The invention relates to compounds of the general formula 
                         
wherein Ar 1 , Ar 2 , R 4 , R 5 , R 6 , R 7 , R 8 , W, X, a and b have the significances given in the specification, and optionally the enantiomers thereof. The active ingredients have advantageous pesticidal properties. They are especially suitable for controlling parasites on warm-blooded animals.

This application is a National Phase Application under § 371 of International Application Number PCT/EP03/05992 filed on Jun. 6, 2002.

The present invention relates to new aminoacetonitrile compounds of formula

wherein

-   R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl,     C₃-C₆-cycloalkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkylthio, C₁-C₆-alkoxy,     C₃-C₆-cycloalkyloxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl,     halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino or unsubstituted or     substituted phenoxy, whereby the substituents may be independent of     one another and are selected from the group consisting of halogen,     nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy,     halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl     and halo-C₁-C₆-alkylsulfonyl; -   R₂ signifies hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,     halo-C₁-C₆-alkyl, C₁-C₆-alkyithio, C₁-C₆-alkoxy,     C₃-C₆-cycloalkyloxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylsulfinyl,     C₁-C₆-alkylsulfonyl, NR₈R₉, hetaryl which is unsubstituted or     substituted once or many times, phenyl which is unsubstituted or     substituted once or many times, whereby the substituents may be     independent of one another and are selected from the group     consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,     C₁-C₆-alkoxy and halo-C₁-C₆-alkoxy; -   R₃, R₄ and R₅ either, independently of one another, signify     hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl; C₃-C₆-cycloalkyl     that is either unsubstituted or substituted once or many times,     whereby the substituents may be independent of one another and are     selected from the group consisting of halogen and C₁-C₆-alkyl;     phenyl that is either unsubstituted or substituted once or many     times, whereby the substituents may be independent of one another     and are selected from the group consisting of halogen, nitro, cyano,     C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,     C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,     halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,     halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino or di-(C₁-C₆-alkyl)amino; -   or R₄ and R₅ together signify C₂-C₆-alkylene; -   R₆ signifies hydrogen, C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl,     C₁-C₆-alkoxy-C₁-C₆-alkyl, aminocarbonyl, C₁-C₆-alkoxycarbonyl,     halo-C₁-C₆-alkylcarbonyl, thio-C₁-C₆-alkylcarbonyl or benzyl; -   R₇ signifies hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,     di(C₁-C₆-alkyl)amino, aryl which is unsubstituted or substituted     once or many times, whereby the substituents may be independent of     one another and are selected from the group consisting of halogen,     nitro, cyano, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₁-C₆-alkyl,     C₁-C₆-alkoxy, C₃-C₆-cycloalkyloxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl,     halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl,     C₂-C₆-alkenyloxy, halo-C₁-C₆-alkenyloxy, C₁-C₆-alkylthio,     halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyloxy,     halo-C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylsulfinyl,     halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,     halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio,     C₂-C₆-alkenylsulfinyi, halo-C₂-C₆-alkenylsulfinyl,     C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino,     di(C₁-C₆-alkyl)amino, C₁-C₆-alkylsulfonylamino,     halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl,     halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,     C₁-C₆-alkylaminocarbonyl, di(C₁-C₆-alkyl)aminocarbonyl;     aryl-C₁-C₆-alkyl which is unsubstituted or substituted once or many     times, arylamino which is unsubstituted or substituted once or many     times, arylcarbonyl which is unsubstituted or substituted once or     many times, arylcarbonyloxy which is unsubstituted or substituted     once or many times, aryloxy which is unsubstituted or substituted     once or many times, aryloxy-C₁-C₆-alkyl which is unsubstituted or     substituted once or many times, hetaryloxy-C₁-C₆-alkyl which is     unsubstituted or substituted once or many times, aryloxycarbonyl     which is unsubstituted or substituted once or many times,     arylsulfonyl which is unsubstituted or substituted once or many     times, arylsulfonylamino which is unsubstituted or substituted once     or many times, pyridyloxy which is unsubstituted or substituted once     or many times, and phenylacetylenyl which is unsubstituted or     substituted once or many times, whereby the substituents may each be     independent of one another and are selected from the group     consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,     C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio,     halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl,     C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; -   hetaryl which is unsubstituted or substituted once or many times,     whereby the substituents may be independent of one another and are     selected from the group consisting of halogen, nitro, cyano,     C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio,     halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl,     C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl,     halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl,     halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl,     halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and     di(C₁-C₆-alkyl)amino; or unsubstituted naphthyl or quinolyl, or     naphthyl or quinolyl which is substituted once or many times,     whereby the substituents may be independent of one another and are     selected from the group consisting of halogen, nitro, cyano,     C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio,     halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl,     C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl,     halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl and     halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl,     halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino -   R₈ and R₉, independently of one another, signify hydrogen,     C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl,     C₁-C₆-alkylthiocarbonyl, thio-C₁-C₆-alkylcarbonyl, aryl or hetaryl; -   Y signifies a direct bond, C(O), C(S) or S(O)_(n); -   a signifies 1, 2 or 3; and -   n is 1 or 2;     their preparation and use in the control of endo- and ectoparasites,     especially helminths, in and on warm-blooded productive livestock     and domestic animals and plants, and furthermore pesticides     containing at least one of these compounds.

Substituted aminoacetonitrile compounds having pesticidal activity are described for example in EP-0.953.565 A2. However, the active ingredients specifically disclosed therein cannot always fulfil the requirements regarding potency and activity spectrum. There is therefore a need for active ingredients with improved pesticidal properties. It has now been found that the aminoacetonitrile compounds of formula I have excellent pesticidal properties, especially against endo- and ecto-parasites in and on productive livestock and domestic animals and plants.

Aryl is phenyl or naphthyl.

Hetaryl is pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl, furanyl, pyrryl, pyrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl, indolyl or indazolyl, preferably pyridyl, pyrimidyl, s-triazinyl or 1,2,4-triazinyl, especially pyridyl or pyrimidyl.

Alkyl—as a group per se and as structural element of other groups and compounds, for example halogen-alkyl, alkoxy, and alkylthio—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, either straight-chained, i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl.

Alkenyl—as a group per se and as structural element of other groups and compounds—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question and of the conjugated or isolated double bonds—either straight-chained, e.g. allyl, 2-butenyl, 3-pentenyl, 1-hexenyl or 1,3-hexadienyl, or branched, e.g. isopropenyl, isobutenyl, isoprenyl, tert.-pentenyl or isohexenyl.

Alkinyl—as a group per se and as structural element of other groups and compounds—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question and of the conjugated or isolated double bonds—either straight-chained, e.g. propargyl, 2-butinyl, 3-pentinyl, 1-hexinyl, 1-heptinyl or 3-hexen-1-inyl, or branched, e.g. 3-methylbut-1-inyl, 4-ethylpent-1-inyl or 4-methylhex-2-inyl.

Cycloalkyl—as a group per se and as structural element of other groups and compounds such as halocycloalkyl,—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Halogen—as a group per se and as structural element of other groups and compounds such as haloalkyl, haloalkoxy and haloalkylthio—is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, in particular fluorine or chlorine.

Halogen-substituted carbon-containing groups and compounds, such as haloalkyl, haloalkoxy or haloalkylthio, may be partially halogenated or perhalogenated, whereby in the case of multiple halogenation, the halogen substituents may be identical or different. Examples of halogen-alkyl—as a group per se and as structural element of other groups and compounds such as haloalkoxy or haloalkylthio,—are methyl which is mono- to trisubstituted by fluorine, chlorine and/or bromine, such as CHF₂ or CF₃; ethyl which is mono- to pentasubstituted by fluorine, chlorine and/or bromine, such as CH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂, CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂, CF₂CHClF, CF₂CHBrF or CClFCHClF; propyl or isopropyl, mono- to heptasubstituted by fluorine, chlorine and/or bromine, such as CH₂CHBrCH₂Br, CF₂CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂; butyl or one of its isomers, mono- to nonasubstituted by fluorine, chlorine and/or bromine, such as CF(CF₃)CHFCF₃ or CH₂(CF₂)₂CF₃; pentyl or one of its isomers substituted once to eleven times by fluorine, chlorine and/or bromine, such as CF(CF₃)(CHF)₂CF₃ or CH₂(CF₂)₃CF₃; and hexyl or one of its isomers substituted once to thirteen times by fluorine, chlorine and/or bromine, such as (CH₂)₄CHBrCH₂Br, CF₂(CHF)₄CF₃, CH₂(CF₂)₄CF₃ or C(CF₃)₂(CHF)₂CF₃.

Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy and tert.-butoxy, as well as the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy. Haloalkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Haloalkoxy is e.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

Alkylthio groups preferably have a chain length of 1 to 6 carbon atoms. Alkylthio is for example methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec.-butylthio or tert.-butylthio, preferably methylthio and ethylthio.

Preferred embodiments within the scope of the invention are:

-   (1) A compound of formula I, wherein R₁ signifies hydrogen, halogen,     cyano, nitro, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy,     halo-C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl,     C₁-C₄-alkylsulfonyl or unsubstituted or substituted phenoxy, whereby     the substituents may be independent of one another and are selected     from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl,     halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy; -   especially hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl,     halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy or unsubstituted     or substituted phenoxy, whereby the substituents may be independent     of one another and are selected from the group consisting of     halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and     halo-C₁-C₄-alkoxy; -   most particularly hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl,     halo-C₁-C₂-alkyl, C₁-C₂-alkoxy or halo-C₁-C₂-alkoxy; -   (2) A compound of formula I, wherein R₂ signifies hydrogen,     C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkylthio, C₁-C₄-alkoxy,     halo-C₁-C₄-alkoxy or C₁-C₄-alkylsulfonyl; -   especially hydrogen, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy or     halo-C₁-C₂-alkoxy; -   most particularly hydrogen, methyl or halomethyl; -   (3) A compound of formula I, wherein R₃, R₄ and R₅, independently of     one another, are hydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,     C₃-C₆-cycloalkyl; phenyl that is either unsubstituted or substituted     once or many times, whereby the substituents may be independent of     one another and are selected from the group consisting of halogen,     nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy,     halo-C₁-C₄-alkoxy; C₁-C₄-alkylthio and halo-C₁-C₄-alkylthio; or R₄     and R₅ together are C₂-C₆-alkylene; -   especially, independently of one another, hydrogen, halogen,     C₁-C₂-alkyl, halo-C₁-C₂-alkyl or C₃-C₆-cycloalkyl; -   most particularly, independently of one another, hydrogen, methyl or     halomethyl;

(4) A compound of formula I, wherein R₆ is hydrogen, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxy-C₁-C₆alkyl or benzyl;

-   especially hydrogen, C₁-C₂-alkyl, C₁-C₂-alkylcarbonyl or benzyl; -   most particularly hydrogen or C₁-C₂-alkyl;

(5) A compound of formula I, wherein R₇ signifies aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkinyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyloxy, halo-C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylsulfonyl, halo-C₁-C₄-alkylsulfonyl, C₂-C₄-alkenylsulfonyl, halo-C₂-C₄-alkenylsulfonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxycarbonyl; aryl-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, aryloxy which is unsubstituted or substituted once or many times, aryloxy-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, hetaryloxy-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, aryloxycarbonyl which is unsubstituted or substituted once or many times, arylsulfonyl which is unsubstituted or substituted once or many times, and pyridyloxy which is unsubstituted or substituted once or many times, whereby the substituents may each be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl and halo-C₁-C₄-alkylsulfonyl;

-   hetaryl which is unsubstituted or substituted once or many times,     whereby the substituents may be independent of one another and are     selected from the group consisting of halogen, nitro, cyano,     C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,     C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio,     halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl and     halo-C₁-C₄-alkylsulfonyl; or -   naphthyl or quinolyl which are unsubstituted or substituted once or     many times, whereby the substituents may be independent of one     another and are selected from the group consisting of halogen,     nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy,     halo-C₁-C₄-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy,     C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₂-C₄-alkenylthio,     halo-C₂-C₄-alkenylthio, C₁-C₄-alkylsulfonyl and     halo-C₁-C₄-alkylsulfonyl; -   in particular aryl which is unsubstituted or substituted once or     many times, whereby the substituents may be independent of one     another and are selected from the group consisting of halogen,     nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy,     halo-C₁-C₂-alkoxy, C₃-C₅-cycloalkyl, C₁-C₂-alkylthio,     halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl, halo-C₁-C₂-alkylsulfonyl,     C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl;     aryl-C₁-C₂-alkyl which is unsubstituted or substituted once or many     times, aryloxy which is unsubstituted or substituted once or many     times, aryloxy-C₁-C₂-alkyl which is unsubstituted or substituted     once or many times, and pyridyloxy which is unsubstituted or     substituted once or many times, whereby the substituents may be     independent of one another and are selected from the group     consisting of halogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl,     C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₁-C₂-alkylthio,     halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl and     halo-C₁-C₂-alkylsulfonyl; or -   hetaryl which is unsubstituted or substituted once or many times,     whereby the substituents may be independent of one another and are     selected from the group consisting of halogen, nitro, cyano,     C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy,     C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₂-alkylthio,     halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl and     halo-C₁-C₂-alkylsulfonyl; -   most particularly aryl which is unsubstituted or substituted once or     many times, whereby the substituents may be independent of one     another and are selected from the group consisting of halogen,     cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy,     halo-C₁-C₂-alkoxy, C₃-C₅-cycloalkyl, C₁-C₂-alkylcarbonyl,     halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl; aryl-C₁-C₂-alkyl     which is unsubstituted or substituted once or many times, and     aryloxy-C₁₋₂-alkyl which is unsubstituted or substituted once or     many times, whereby the substituents may each be independent of one     another and are selected from the group consisting of halogen,     cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy and     halo-C₁-C₂-alkoxy, -   (6) a compound of formula I, wherein R₈ and R₉ independently of one     another, signify hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl,     C₁-C₆-alkylcarbonyl or aryl; -   especially, independently of one another, hydrogen or C₁-C₄-alkyl; -   especially, independently of one another, hydrogen or C₁-C₂-alkyl; -   (7) A compound of formula I, wherein Y is C(O) or S(O)_(n); -   especially C(O); -   (8) A compound of formula I, wherein a is 1 or 2; -   especially 1; -   (9) A compound of formula I, wherein n is 2; -   (10) A compound of formula I, wherein -   R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl,     halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,     C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl     or unsubstituted or substituted phenoxy, whereby the substituents     may be independent of one another and are selected from the group     consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,     C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy; -   R₂ is hydrogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkylthio,     C₁-C₄-alkoxy or C₁-C₄-alkylsulfonyl; -   R₃, R₄ and R₅, independently of one another, are hydrogen, halogen,     C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl; phenyl that is     either unsubstituted or substituted once or many times, whereby the     substituents may be independent of one another and are selected from     the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl,     halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy; C₁-C₄-alkylthio     and halo-C₁-C₄-alkylthio; or R₄ and R₅ together are C₂-C₆-alkylene; -   R₆ is hydrogen, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl,     C₁-C₆-alkoxy-C₁-C₆-alkyl or benzyl; -   R₇ signifies aryl which is unsubstituted or substituted once or many     times, whereby the substituents may be independent of one another     and are selected from the group consisting of halogen, nitro, cyano,     C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,     C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkinyl, C₃-C₆-cycloalkyl,     C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio,     halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyloxy,     halo-C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylsulfonyl,     halo-C₁-C₄-alkylsulfonyl, C₂-C₄-alkenylsulfonyl,     halo-C₂-C₄-alkenylsulfonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,     C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxycarbonyl;     aryl-C₁-C₄-alkyl which is unsubstituted or substituted once or many     times, aryloxy which is unsubstituted or substituted once or many     times, aryloxy-C_(1-C) ₄-alkyl which is unsubstituted or substituted     once or many times, hetaryloxy-C₁-C₄-alkyl which is unsubstituted or     substituted once or many times, aryloxycarbonyl which is     unsubstituted or substituted once or many times, arylsulfonyl which     is unsubstituted or substituted once or many times, and pyridyloxy     which is unsubstituted or substituted once or many times, whereby     the substituents may each be independent of one another and are     selected from the group consisting of halogen, nitro, cyano,     C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,     C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl and     halo-C₁-C₄-alkylsulfonyl; -   hetaryl which is unsubstituted or substituted once or many times,     whereby the substituents may be independent of one another and are     selected from the group consisting of halogen, nitro, cyano,     C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,     C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio,     halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl and     halo-C₁-C₄-alkylsulfonyl; or -   naphthyl or quinolyl which are unsubstituted or substituted once or     many times, whereby the substituents may be independent of one     another and are selected from the group consisting of halogen,     nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy,     halo-C₁-C₄-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy,     C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₂-C₄-alkenylthio,     halo-C₂-C₄-alkenylthio, C₁-C₄-alkylsulfonyl and     halo-C₁-C₄-alkylsulfonyl; -   R₈ and R₉ independently of one another, signify hydrogen,     C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl or aryl; -   Y is C(O) or S(O)_(n); -   a signifies 1 or 2; and -   n signifies 2; -   (11) A compound of formula I, wherein -   R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl,     halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy or unsubstituted     or substituted phenoxy, whereby the substituents may be independent     of one another and are selected from the group consisting of     halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and     halo-C₁-C₄-alkoxy; -   R₂ signifies hydrogen, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy     or halo-C₁-C₂-alkoxy; -   R₃, R₄ and R₅, independently of one another, signify hydrogen,     halogen, C₁-C₂-alkyl, halo-C₁-C₂-alkyl or C₃-C₆-cycloalkyl; -   R₆ signifies hydrogen, C₁-C₂-alkyl, C₁-C₂-alkylcarbonyl or benzyl; -   R₇ signifies aryl which is unsubstituted or substituted once or many     times, whereby the substituents may be independent of one another     and are selected from the group consisting of halogen, nitro, cyano,     C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy,     C₃-C₅-cycloalkyl, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio,     C₁-C₂-alkylsulfonyl, halo-C₁-C₂-alkylsulfonyl, C₁-C₂-alkylcarbonyl,     halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl; aryl-C₁-C₂-alkyl     which is unsubstituted or substituted once or many times, aryloxy     which is unsubstituted or substituted once or many times,     aryloxy-C₁-C₂-alkyl which is unsubstituted or substituted once or     many times, and pyridyloxy which is unsubstituted or substituted     once or many times, whereby the substituents may be independent of     one another and are selected from the group consisting of halogen,     nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy,     halo-C₁-C₂-alkoxy, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio,     C₁-C₂-alkylsulfonyl and halo-C₁-C₂-alkylsulfonyl; or -   hetaryl which is unsubstituted or substituted once or many times,     whereby the substituents may be independent of one another and are     selected from the group consisting of halogen, nitro, cyano,     C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy,     C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₂-alkylthio,     halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl and     halo-C₁-C₂-alkylsulfonyl; -   R₈ and R₉, independently of one another, signify hydrogen or     C₁-C₄-alkyl; -   Y signifies C(O); -   a signifies 1; and -   n signifies 2;

(12) A compound of formula I, wherein

-   R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl,     halo-C₁-C₂-alkyl, C₁-C₂-alkoxy or halo-C₁-C₂-alkoxy; -   R₂ is hydrogen, methyl or halomethyl; -   R₃, R₄ and R₅, independently of one another, signify hydrogen,     methyl or halomethyl; -   R₆ signifies hydrogen or C₁-C₂-alkyl; -   R₇ signifies aryl which is unsubstituted or substituted once or many     times, whereby the substituents may be independent of one another     and are selected from the group consisting of halogen, cyano,     C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy,     C₃-C₅-cycloalkyl, C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl,     C₁-C₂-alkoxycarbonyl; aryl-C₁-C₂-alkyl which is unsubstituted or     substituted once or many times, and aryloxy-C₁-C₂-alkyl which is     unsubstituted or substituted once or many times, whereby the     substituents may each be independent of one another and are selected     from the group consisting of halogen, cyano, C₁-C₂-alkyl,     halo-C₁-C₂-alkyl, C₁-C₂-alkoxy and halo-C₁-C₂-alkoxy; -   R₈ and R₉, independently of one another, signify hydrogen or     C₁-C₂-alkyl; -   Y signifies C(O); -   a signifies 1; and -   n is 2.

Within the context of the invention, particular preference is given to the compounds of formula I listed in Table 1, and most particularly those named in the synthesis examples.

A further object of the invention is the process for the preparation of the compounds of formula I, respectively in free form or in salt form, for example characterised in that a compound of formula

which is known or may be produced analogously to corresponding known compounds, and wherein R₁, R₂, R₃, R₄, R₅, R₆ and a are defined as given for formula I, is reacted with a compound of formula Q—Y—R₇  III, which is known or may be prepared analogously to corresponding known compounds, and wherein Y and R₇ are defined as given for formula I and Q is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula I obtainable according to the method or in another way, respectively in free form or in salt form, is converted into another compound of formula I, a mixture of isomers obtainable according to the method is separated and the desired isomer isolated and/or a free compound of formula I obtainable according to the method is converted into a salt or a salt of a compound of formula I obtainable according to the method is converted into the free compound of formula I or into another salt.

What has been stated above for salts of compounds I also applies analogously to salts of the starting materials listed hereinabove and hereinbelow.

The reaction partners can be reacted with one another as they are, i.e. without the addition of a solvent or diluent, e.g. in the melt. In most cases, however, the addition of an inert solvent or diluent, or a mixture thereof, is of advantage. Examples of such solvents or diluents are: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetraline, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloroethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethylether, dimethoxydiethylether, tetrahydrofuran or dioxane; ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone; amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide.

Preferred leaving groups are halogens, especially chlorine.

Suitable bases for facilitating the reaction are e.g. alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkylamides or alkylsilylamides; alkylamines, alkylenediamines, optionally N-alkylated, optionally unsaturated, cycloalkylamines, basic heterocycles, ammonium hydroxides, as well as carbocyclic amines. Those which may be mentioned by way of example are sodium hydroxide, hydride, amide, methanolate, acetate, carbonate, potassium tert.-butanolate, hydroxide, carbonate, hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)-amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide, as well as 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU). Preference is given to diisopropylethylamine and 4-(N,N-dimethylamino)pyridine.

The reaction advantageously takes place in a temperature range of ca. 0° C. to ca. 100° C., preferably from ca. 10° C. to ca. 40° C.

In a preferred process, a compound of formula II is reacted at room temperature in a halogenated hydrocarbon, preferably dichloromethane, with a compound of formula III in the presence of a base, preferably a mixture of diisopropylethylamine and 4-(N,N-dimethylamino)pyridine.

A further object of the invention is the process for the preparation of the compounds of formula II, respectively in free form or in salt form, for example characterised in that a compound of formula

which is known or may be produced analogously to corresponding known compounds, in which R₁, R₂, R₃, R₄, R₅ and a are defined as for formula I, is reacted with an inorganic or organic cyanide and a compound of formula R₆—NH₂, which is known or may be produced analogously to corresponding known compounds and wherein R₆ is defined as for formula I, and if desired, a compound of formula II obtainable according to the method or in another way, respectively in free form or in salt form, is converted into another compound of formula II, a mixture of isomers obtainable according to the method is separated and the desired isomer isolated and/or a free compound of formula II obtainable according to the method is converted into a salt or a salt of a compound of formula II obtainable according to the method is converted into the free compound of formula II or into another salt

Suitable cyanides are sodium cyanide, potassium cyanide, trimethylsilyl cyanide and acetone cyanohydrin.

The general method for reacting carbonyl compounds, e.g. of formula IV, with cyanides and amines, e.g. of formula R₆—NH₂, is a Strecker reaction, for example as in Organic Synthesis Coll. Vol. 3, 88 (1973).

Salts of compounds I may be produced in known manner. Acid addition salts of compounds I, for example, are obtainable by treatment with a suitable acid or a suitable ion exchange reagent, and salts with bases are obtainable by treatment with a suitable base or a suitable ion exchange reagent.

Salts of compounds I can be converted into the free compounds I by the usual means, acid addition salts e.g. by treating with a suitable basic composition or with a suitable ion exchange reagent, and salts with bases e.g. by treating with a suitable acid or a suitable ion exchange reagent.

Salts of compounds I can be converted into other salts of compounds I in a known manner; acid addition salts can be converted for example into other acid addition salts, e.g. by treating a salt of an inorganic acid, such as a hydrochloride, with a suitable metal salt, such as a sodium, barium, or silver salt, of an acid, e.g. with silver acetate, in a suitable solvent, in which a resulting inorganic salt, e.g. silver chloride, is insoluble and thus precipitates out from the reaction mixture.

Depending on the method and/or reaction conditions, compounds I with salt-forming characteristics can be obtained in free form or in the form of salts.

Compounds I can also be obtained in the form of their hydrates and/or also can include other solvents, used for example where necessary for the crystallisation of compounds present in solid form.

The compounds I may be optionally present as optical and/or geometric isomers or as a mixture thereof. The invention relates both to the pure isomers and to all possible isomeric mixtures, and is hereinbefore and hereinafter understood as doing so, even if stereochemical details are not specifically mentioned in every case.

Diastereoisomeric mixtures of compounds I, which are obtainable by the process or in another way, may be separated in known manner, on the basis of the physical-chemical differences in their components, into the pure diastereoisomers, for example by fractional crystallisation, distillation and/or chromatography.

Splitting of mixtures of enantiomers, that are obtainable accordingly, into the pure isomers, may be achieved by known methods, for example by recrystallisation from an optically active solvent, by chromatography on chiral adsorbents, e.g. high-pressure liquid chromatography (HPLC) on acetyl cellulose, with the assistance of appropriate micro-organisms, by cleavage with specific immobilised enzymes, through the formation of inclusion compounds, e.g. using chiral crown ethers, whereby only one enantiomer is complexed.

According to the invention, apart from separation of corresponding isomer mixtures, generally known methods of diastereoselective or enantioselective synthesis can also be applied to obtain pure diastereoisomers or enantiomers, e.g. by carrying out the method of the invention using educts with correspondingly suitable stereochemistry.

It is advantageous to isolate or synthesise the biologically more active isomer, e.g. enantiomer, provided that the individual components have differing biological efficacy.

In the method of the present invention, the starting materials and intermediates used are preferably those that lead to the compounds I described at the beginning as being especially useful.

The invention relates especially to the method of preparation described in the example.

Starting materials and intermediates, which are new and are used according to the invention for the preparation of compounds I, as well as their usage and process for the preparation thereof, similarly form an object of the invention.

The compounds I according to the invention are notable for their particularly broad activity spectrum and are valuable active ingredients for use in pest control, including in particular the control of endo- and ecto-parasites on animals, whilst being well-tolerated by warm-blooded animals, fish and plants,

In the context of the present invention, ectoparasites are understood to be in particular insects, mites and ticks. These include insects of the order: Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera. However, the ectoparasites which may be mentioned in particular are those which trouble humans or animals and carry pathogens, for example flies such as Musca domestics, Musca vetustissima, Musca autumnalis, Fannia canicularis, Sarcophaga camada, Lucilia cuprina, Hypoderma bovis, Hypoderma lineatum, Chrysomyia chloropyga, Dermatobia hominis, Cochliomyia hominivorax, Gasterophilus intestinalis, Oestrus ovis, Stomoxys calcitrans, Haematobia irritans and midges (Nematocera), such as Culicidae, Simulmidae, Psychodidae, but also blood-sucking parasites, for example fleas, such as Ctenocephalides felis and Ctenocephalides canis (cat and dog fleas), Xenopsylla cheopis, Pulex irritans, Dermatophilus penetrans, lice, such as Damalina ovis, Pediculus humanis, biting flies and horse-flies (Tabanidae), Haematopota spp. such as Haematopota pluvialis, Tabanidea spp. such as Tabanus nigrovittatus, Chrysopsinae spp. such as Chrysops caecutiens, tsetse flies, such as species of Glossinia, biting insects, particularly cockroaches, such as Blatella germanica, Blatta orientalis, Periplaneta americana, mites, such as Dermanyssus gallinae, Sarcoptes scabiei, Psoroptes ovis and Psorergates spp. and last but not least ticks. The latter belong to the order Acadna. Known representatives of ticks are, for example, Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas, Otobius and Omithodoros and the like, which preferably infest warm-blooded animals including farm animals, such as cattle, pigs, sheep and goats, poultry such as chickens, turkeys and geese, fur-bearing animals such as mink, foxes, chinchillas, rabbits and the like, as well as domestic animals such as cats and dogs, but also humans.

Compounds I can also be used against hygiene pests, especially of the order Diptera of the families Sarcophagidae, Anophilidae and Culicidae; the orders Orthoptera, Dictyoptera (e.g. the family Blattidae) and Hymenoptera (e.g. the family Formicidae).

Compounds I also have sustainable efficacy on parasitic mites and insects of plants. In the case of spider mites of the order Acarina, they are effective against eggs, nymphs and adults of Tetranychidae (Tetranychus spp. and Panonychus spp.).

They have high activity against sucking insects of the order Homoptera, especially against pests of the families Aphididae, Delphacidae, Cicadellidae, Psyllidae, Loccidae, Diaspididae and Eriophydidae (e.g. rust mite on citrus fruits); the orders Hemiptera, Heteroptera and Thysanoptera, and on the plant-eating insects of the orders Lepidoptera, Coleoptera, Diptera and Orthoptera

They are similarly suitable as a soil insecticide against pests in the soil.

The compounds of formula I are therefore effective against all stages of development of sucking insects and eating insects on crops such as cereals, cotton, rice, maize, soya, potatoes, vegetables, fruit, tobacco, hops, citrus, avocados and other crops.

The compounds of formula I are also effective against plant nematodes of the species Meloidogyne, Heterodera, Pratylenchus, Ditylenchus, Radopholus, Rizoglyphus etc.

In particular, the compounds are effective against helminths, in which the endoparasitic nematodes and trematodes may be the cause of serious diseases of mammals and poultry, e.g. sheep, pigs, goats, cattle, horses, donkeys, dogs, cats, guinea-pigs and exotic birds. Typical nematodes of this indication are: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. The trematodes include, in particular, the family of Fasciolideae, especially Fasciola hepatica. It could also be shown surprisingly and unexpectedly that the compounds of formula I have exceptionally high efficacy against nematodes that are resistant to many active substances. This can be demonstrated in vitro by the LDA test and in vivo for example in Mongolian gerbils and sheep. It was shown that amounts of active substance which kill sensitive strains of Haemonchus contortus or Trichostrongylus colubriformis, are also sufficiently effective at controlling corresponding strains that are resistant to benzimidazoles, levamisol and macrocyclic lactones (for example ivermectin).

Certain pests of the species Nematodirus, Cooperia and Oesophagostonum infest the intestinal tract of the host animal, while others of the species Haemonchus and Ostertagia are parasitic in the stomach and those of the species Dictyocaulus are parasitic in the lung tissue. Parasites of the families Filariidae and Setariidae may be found in the internal cell tissue and in the organs, e.g. the heart, the blood vessels, the lymph vessels and the subcutaneous tissue. A particularly notable parasite is the heartworm of the dog, Dirofilaria immitis. The compounds of formula I are highly effective against these parasites.

Furthermore, the compounds of formula I are suitable for the control of human pathogenic parasites. Of these, typical representatives that appear in the digestive tract are those of the species Ancylostoma, Necator, Ascaris, Strongyloides, Trichinella, Capillaria, Trichuris and Enterobius. The compounds of the present invention are also effective against parasites of the species Wuchereria, Brugia, Onchocerca and Loa from the family of Filariidae, which appear in the blood, in the tissue and in various organs, and also against Dracunculus and parasites of the species Strongyloides and Trichinella, which infect the gastrointestinal tract in particular.

The good pesticidal activity of the compounds of formula I according to the invention corresponds to a mortality rate of at least 50-60% of the pests mentioned. In particular, the compounds of formula I are notable for the exceptionally long duration of efficacy.

The compounds of formula I are preferably employed in unmodified form or preferably together with the adjuvants conventionally used in the art of formulation and may therefore be processed in a known manner to give, for example, emulsifiable concentrates, directly dilutable solutions, dilute emulsions, soluble powders, granules or microencapsulations in polymeric substances. As with the compositions, the methods of application are selected in accordance with the intended objectives and the prevailing circumstances.

The formulation, i.e. the agents, preparations or compositions containing the active ingredient of formula I, or combinations of these active ingredients with other active ingredients, and optionally a solid or liquid adjuvant, are produced in a manner known per se, for example by intimately mixing and/or grinding the active ingredients with spreading compositions, for example with solvents, solid carriers, and optionally surface-active compounds (surfactants).

The solvents in question may be: alcohols, such as ethanol, propanol or butanol, and glycols and their ethers and esters, such as propylene glycol, dipropylene glycol ether, ethylene glycol, ethylene glycol monomethyl or -ethyl ether, ketones, such as cyclohexanone, isophorone or diacetanol alcohol, strong polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, or water, vegetable oils, such as rape, castor, coconut, or soybean oil, and also, if appropriate, silicone oils.

Preferred application forms for usage on warm-blooded animals in the control of helminths include solutions, emulsions, suspensions (drenches), food additives, powders, tablets including effervescent tablets, boll, capsules, micro-capsules and pour-on formulations, whereby the physiological compatibility of the formulation excipients must be taken into consideration.

The binders for tablets and boll may be chemically modified polymeric natural substances that are soluble in water or in alcohol, such as starch, cellulose or protein derivatives (e.g. methyl cellulose, carboxymethyl cellulose, ethylhydroxyethyl cellulose, proteins such as zein, gelatin and the like), as well as synthetic polymers, such as polyvinyl alcohol, polyvinyl pyrrolidone etc. The tablets also contain fillers (e.g. starch, microcrystalline cellulose, sugar, lactose etc.), glidants and disintegrants.

If the anthelminthics are present in the form of feed concentrates, then the carriers used are e.g. performance feeds, feed grain or protein concentrates. Such feed concentrates or compositions may contain, apart from the active ingredients, also additives, vitamins, antibiotics, chemotherapeutics or other pesticides, primarily bacteriostats, fungistats, coccidiostats, or even hormone preparations, substances having anabolic action or substances which promote growth, which affect the quality of meat of animals for slaughter or which are beneficial to the organism in another way. If the compositions or the active ingredients of formula I contained therein are added directly to feed or to the drinking troughs, then the formulated feed or drink contains the active ingredients preferably in a concentration of ca. 0.0005 to 0.02% by weight (5-200 ppm).

The compounds of formula I according to the invention may be used alone or in combination with other biocides. They may be combined with pesticides having the same sphere of activity e.g. to increase activity, or with substances having another sphere of activity e.g. to broaden the range of activity. It can also be sensible to add so-called repellents. If the range of activity is to be extended to endoparasites, e.g. wormers, the compounds of formula I are suitably combined with substances having endoparasitic properties. Of course, they can also be used in combination with antibacterial compositions. Since the compounds of formula I are adulticides, i.e. since they are effective in particular against the adult stages of the target parasites, the addition of pesticides which instead attack the juvenile stages of the parasites may be very advantageous. In this way, the greatest part of those parasites that produce great economic damage will be covered. Moreover, this action will contribute substantially to avoiding the formation of resistance. Many combinations may also lead to synergistic effects, i.e. the total amount of active ingredient can be reduced, which is desirable from an ecological point of view. Preferred groups of combination partners and especially preferred combination partners are named in the following, whereby combinations may contain one or more of these partners in addition to a compound of formula I.

Suitable partners in the mixture may be biocides, e.g. the insecticides and acaricides with a varying mechanism of activity, which are named in the following and have been known to the person skilled in the art for a long time, e.g. chitin synthesis inhibitors, growth regulators; active ingredients which act as juvenile hormones; active ingredients which act as adulticides; broad-band insecticides, broad-band acaricides and nematicides; and also the well known anthelminthics and insect- and/or acarid-deterring substances, said repellents or detachers.

Non-limitative examples of suitable insecticides and acaricides are:

1. Abamectin 2. AC 303 630 3. Acephat 4. Acrinathrin 5. Alanycarb 6. Aldicarb 7. α-Cypermethrin 8. Alphamethrin 9. Amitraz 10. Avermectin B₁ 11. AZ 60541 12. Azinphos A 13. Azinphos M 14. Azocyclotin 15. Bacillus subtil. toxin 16. Bendiocarb 17. Benfuracarb 18. Bensultap 19. β-Cyfluthrin 20. Bifenthrin 21. BPMC 22. Brofenprox 23. Bromophos A 24. Bufencarb 25. Buprofezin 26. Butocarboxim 27. Butylpyridaben 28. Cadusafos 29. Carbaryl 30. Carbofuran 31. Carbophenothion 32. Cartap 33. Cloethocarb 34. Chlorethoxyfos 35. Chlorfenapyr 36. Chlorfluazuron 37. Chlormephos 38. Chlorpyrifos 39. Cis-Resmethrin 40. Clocythrin 41. Clofentezin 42. Cyanophos 43. Cycloprothrin 44. Cyfluthrin 45. Cyhexatin 46. D 2341 47. Deltamethrin 48. Demeton M 49. Demeton S 50. Demeton-S-methyl 51. Dichlofenthion 52. Dicliphos 53. Diethion 54. Diflubenzuron 55. Dimethoat 56. Dimethylvinphos 57. Dioxathion 58. DPX-MP062 59. Edifenphos 60. Emamectin 61. Endosulfan 62. Esfenvalerat 63. Ethiofencarb 64. Ethion 65. Ethofenprox 66. Ethoprophos 67. Etrimfos 68. Fenamiphos 69. Fenazaquin 70. Fenbutatinoxid 71. Fenitrothion 72. Fenobucarb 73. Fenothiocarb 74. Fenoxycarb 75. Fenpropathrin 76. Fenpyrad 77. Fenpyroximate 78. Fenthion 79. Fenvalerate 80. Fipronil 81. Fluazinam 82. Fluazuron 83. Flucycloxuron 84. Flucythrinat 85. Flufenoxuron 86. Flufenprox 87. Fonofos 88. Formothion 89. Fosthiazat 90. Fubfenprox 91. HCH 92. Heptenophos 93. Hexaflumuron 94. Hexythiazox 95. Hydroprene 96. Imidacloprid 97. insect-active fungi 98. insect-active nematodes 99. insect-active viruses 100. Iprobenfos 101. Isofenphos 102. Isoprocarb 103. Isoxathion 104. Ivermectin 105. λ-Cyhalothrin 106. Lufenuron 107. Malathion 108. Mecarbam 109. Mesulfenfos 110. Metaldehyd 111. Methamidophos 112. Methiocarb 113. Methomyl 114. Methoprene 115. Metolcarb 116. Mevinphos 117. Milbemectin 118. Moxidectin 119. Naled 120. NC 184 121. NI-25, Acetamiprid 122. Nitenpyram 123. Omethoat 124. Oxamyl 125. Oxydemeton M 126. Oxydeprofos 127. Parathion 128. Parathion-methyl 129. Permethrin 130. Phenthoat 131. Phorat 132. Phosalone 133. Phosmet 134. Phoxim 135. Pirimicarb 136. Pirimiphos A 137. Pirimiphos M 138. Promecarb 139. Propaphos 140. Propoxur 141. Prothiofos 142. Prothoat 143. Pyrachlofos 144. Pyradaphenthion 145. Pyresmethrin 146. Pyrethrum 147. Pyridaben 148. Pyrimidifen 149. Pyriproxyfen 150. RH 5992 151. RH-2485 152. Salithion 153. Sebufos 154. Silafluofen 155. Spinosad 156. Sulfotep 157. Sulprofos 158. Tebufenozide 159. Tebufenpyrad 160. Tebupirimfos 161. Teflubenzuron 162. Tefluthrin 163. Temephos 164. Terbam 165. Terbufos 166. Tetrachlorvinphos 167. Thiafenox 168. Thiodicarb 169. Thiofanox 170. Thionazin 171. Thuringiensin 172. Tralomethrin 173. Triarathene 174. Triazamate 175. Triazophos 176. Triazuron 177. Trichlorfon 178. Triflumuron 179. Trimethacarb 180. Vamidothion 181. XMC (3,5,-Xylyl- methylcarbamate) 182. Xylylcarb 183. YI 5301/5302 184. ζ-Cypermethrin 185. Zetamethrin

Non-limitative examples of suitable anthelminthics are named in the following, a few representatives have insecticidal and acaricidal activity in addition to the anthelminthic activity, and are partly already in the above list.

-   (A1)     Praziquantel=2-cyclohexlcarbonyl-4-1,2,3,6,7,11b-hexahydro-4H-pryrazino[2,1-α]isoquinolin -   (A2)     Closantel=3,5-diiodo-N-[5-chloro-2-methyl-4-(a-cyano-4-chlorobenzyl)phenyl]-salicylamide -   (A3)     Triclabendazole=5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole -   (A4)     Levamisol=L-(−)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1b]thiazole -   (A5) Mebendazole=(5-benzoyl-1H-benzimidazol-2-yl)carbaminic acid     methylester -   (A6) Omphalotin=a macrocyclic fermentation product of the fungus     Omphalotus olearius described in WO 97/20857 -   (A7) Abamectin=avemectin B1 -   (A8) Ivermectin=22,23-dihydroavermectin B1 -   (A9)     Moxidectin=5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-milbemycin     B -   (A10)     Doramectin=25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectin     A1a -   (A11) Milbemectin=mixture of milbemycin A3 and A4 -   (A12) Milbemycinoxim=5-oxime of milbemectin

Non-limitative examples of suitable repellents and detachers are:

-   (R1) DEET (N,N-diethyl-m-toluamide) -   (R2) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)-piperidine -   (R3)     Cymiazole=N,-2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene-2,4-xylidene

The said partners in the mixture are best known to specialists in this field. Most are described in various editions of the Pesticide Manual, The British Crop Protection Council, London, and others in the various editions of The Merck Index, Merck & Co., Inc., Rahway, N.J., USA or in patent literature. Therefore, the following listing is restricted to a few places where they may be found by way of example.

-   (I) 2-Methyl-2-(methylthio)propionaldehyde-O-methylcarbamoyloxime     (Aldicarb), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 26; -   (II)     S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl)O,O-dimethyl-phosphorodithioate     (Azinphos-methyl), from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 67; -   (III)     Ethyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl-(methyl)aminothio]-N-isopropyl-β-alaninate     (Benfuracarb), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 96; -   (IV)     2-Methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate     (Bifenthrin), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 118; -   (V) 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazian-4-one     (Buprofezin), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 157; -   (VI) 2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate     (Carbofuran), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 186; -   (VII)     2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-(dibutylaminothio)methylcarbamate     (Carbosulfan), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 188; -   (VIII) S,S′-(2-dimethylaminotrimethylene)-bis(thiocarbamate)     (Cartap), from The Pesticide Manual, 11^(th) Ed. (1997), The British     Crop Protection Council, London, page 193; -   (IX)     1-[3,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluoro     -benzoyl)-urea (Chlorfluazuron), from The Pesticide Manual, 11^(th)     Ed. (1997), The British Crop Protection Council, London, page 213; -   (X) O,O-diethyl-O-3,5,6-trichloro-2-pyridyl-phosphorothioate     (Chlorpyrifos), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 235; -   (XI)     (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS,1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-di-methylcyclopropanecarboxylate     (Cyfluthrin), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 293; -   (XII) Mixture of     (S)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate     and     (R)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate     (Lambda-Cyhalothrin), from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 300; -   (XIII) Racemate consisting of     (S)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     and     (R)-α-cyano-3-phenoxybenzyl-(1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     (Alpha-cypermethrin), from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 308; -   (XIV) a mixture of the stereoisomers of (S)-α-cyano-3-phenoxybenzyl     (1RS,3RS,-1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     (zeta-Cypermethrin), from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 314; -   (XV)     (S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate     (Deltamethrin), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 344; -   (XVI) (4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (Diflubenzuron),     from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop     Protection Council, London, page 395; -   (XVII)     (1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene)-sulphite     (Endosulfan), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 459; -   (XVIII) α-ethylthio-o-tolyl-methylcarbamate (Ethiofencarb), from The     Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection     Council, London, page 479; -   (XIX) O,O-dimethyl-O-4-nitro-m-tolyl-phosphorothioate     (Fenitrothion), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 514; -   (XX) 2-sec-butylphenyl-methylcarbamate (Fenobucarb), from The     Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection     Council, London, page 516; -   (XXI)     (RS)-α-cyano-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methylbutyrate     (Fenvalerate), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 539; -   (XXII)     S-[formyl(methyl)carbamoylmethyl]-O,O-dimethyl-phosphorodithioate     (Formothion), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 625; -   (XXIII) 4-Methylthio-3,5-xylyl-methylcarbamate (Methiocarb), from     The Pesticide Manual, 11^(th) Ed. (1997), The British Crop     Protection Council, London, page 813; -   (XXIV) 7-Chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl-dimethylphosphate     (Heptenophos), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 670; -   (XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine     (Imidacloprid), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 706; -   (XXVI) 2-isopropylphenyl-methylcarbamate (Isoprocarb), from The     Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection     Council, London, page 729; -   (XXVII) O,S-dimethyl-phosphoramidothioate (Methamidophos), from The     Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection     Council, London, page 808; -   (XXVIII) S-Methyl-N-(methylcarbamoyloxy)thioacetimidate (Methomyl),     from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop     Protection Council, London, page 815; -   (XXIX) Methyl-3-(dimethoxyphosphinoyloxy)but-2-enoate (Mevinphos),     from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop     Protection Council, London, page 844; -   (XXX) O,O-diethyl-O-4-nitrophenyl-phosphorothioate (Parathion), from     The Pesticide Manual, 11^(th) Ed. (1997), The British Crop     Protection Council, London, page 926; -   (XXXI) O,O-dimethyl-O-4-nitrophenyl-phosphorothioate     (Parathion-methyl), from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 928; -   (XXXII)     S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-O,O-diethyl-phosphordithioate     (Phosalone), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 963; -   (XXXIII)     2-Dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate     (Pirimicarb), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 985; -   (XXXIV) 2-isopropoxyphenyl-methylcarbamate (Propoxur), from The     Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection     Council, London, page 1036; -   (XXXV)     1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea     (Teflubenzuron), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1158; -   (XXXVI) S-tert-butylthiomethyl-O,O-dimethyl-phosphorodithioate     (Terbufos), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1165; -   (XXXVII)     ethyl-(3-tert.-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazol-5-yl-thio)-acetate,     (Triazamate), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1224; -   (XXXVIII) Abamectin, from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 3; -   (XXXIX) 2-sec-butylphenyl-methylcarbamate (Fenobucarb), from The     Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection     Council, London, page 516; -   (XL) N-tert.-butyl-N-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide     (Tebufenozide), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1147; -   (XLI)     (±)-5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethyl-sulphinylpyrazol-3-carbonitrile     (Fipronil), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 545; -   (XLII)     (RS)-α-cyano-4-fluoro-3-phenoxybenzyl(1RS,3RS,1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     (beta-Cyfluthrin), from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 295; -   (XLIII)     (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane     (Silafluofen), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1105; -   (XLIV) tert.-butyl     (E)-α-(1,3-dimethyl-5-phenoxypyrazol-4-yl-methylenamino-oxy)-p-toluate     (Fenpyroximate), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 530; -   (XLV)     2-tert.-butyl-5-(4-tert.-butylbenzylthio)-4-chloropyridazin-3(2H-one     (Pyridaben), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1161; -   (XLVI) 4-[[4-(1,1-dimethylphenyl)phenyl]ethoxy]-uinazoline     (Fenazaquin), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 507; -   (XLVII) 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyl-ether     (Pyriproxyfen), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1073; -   (XLVIII)     5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethyl}-6-ethylpyrimidine-4-amine     (Pyrimidifen), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1070; -   (XLIX)     (E)-N(6-chloro-3-pyridylmethyl)-N-ethyl-N-methyl-2-nitrovinylidenediamine     (Nitenpyram), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 880; -   (L)     (E)-N¹-[(6-chloro-3-pyridyl)methyl]-N²-cyano-N¹-methylacetamidine     (NI-25, Acetamiprid), from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 9; -   (LI) Avermectin B₁, from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 3; -   (LII) an insect-active extract from a plant, especially     (2R,6aS,12aS)-1,2,6,6a,12,12a-hexhydro-2-isopropenyl-8,9-dimethoxy-chromeno[3,4-b]furo[2,3-h]chromen-6-one     (Rotenone), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 1097; and an extract     from Azadirachta indica, especially azadirachtin, from The Pesticide     Manual, 11^(th) Ed. (1997), The British Crop Protection Council,     London, page 59; and -   (LIII) a preparation which contains insect-active nematodes,     preferably Heterorhabditis bacteriophora and Heterorhabditis     megidis, from The Pesticide Manual, 11^(th) Ed. (1997), The British     Crop Protection Council, London, page 671; Steinernema feltiae, from     The Pesticide Manual, 11^(th) Ed. (1997), The British Crop     Protection Council, London, page 1115 and Steinemema scapterisci,     from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop     Protection Council, London, page 1116; -   (LIV) a preparation obtainable from Bacillus subtilis, from The     Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection     Council, London, page 72; or from a strain of Bacillus thuringiensis     with the exception of compounds isolated from GC91 or from     NCTC11821; The Pesticide Manual, 11^(th) Ed. (1997), The British     Crop Protection Council, London, page 73; -   (LV) a preparation which contains insect-active fungi, preferably     Verticillium lecanii, from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 1266; Beauveria     brogniartii, from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 85 and Beauveria     bassiana, from The Pesticide Manual, 11^(th) Ed. (1997), The British     Crop Protection Council, London, page 83; -   (LVI) a preparation which contains insect-active viruses, preferably     Neodipridon Sertifer NPV, from The Pesticide Manual, 11^(th) Ed.     (1997), The British Crop Protection Council, London, page 1342;     Mamestra brassicae NPV, from The Pesticide Manual, 11^(th) Ed.     (1997), The British Crop Protection Council, London, page 759 and     Cydia pomonella granulosis virus, from The Pesticide Manual, 11^(th)     Ed. (1997), The British Crop Protection Council, London, page 291; -   (CLXXXI)     7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)-carbamoyl]indol[1,2e]oxazoline-4a-carboxylate     (DPX-MP062, Indoxycarb), from The Pesticide Manual, 11^(th) Ed.     (1997), The British Crop Protection Council, London, page 453; -   (CLXXXII)     N′-tert.-butyl-N′-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide     (RH-2485, Methoxyfenozide), from The Pesticide Manual, 11^(th) Ed.     (1997), The British Crop Protection Council, London, page 1094; and -   (CLXXXIII) (N′-[4-methoxy-biphenyl-3-yl]-hydrazinecarboxylic acid     isopropylester (D 2341), from Brighton Crop Protection Conference,     1996, 487-493; -   (R2) Book of Abstracts, 212th ACS National Meeting Orlando, Fla.,     Aug. 25-29 (1996), AGRO-020. Publisher: American Chemical Society,     Washington, D.C. CONEN: 63BFAF.

As a consequence of the above details, a further essential aspect of the present invention relates to combination preparations for the control of parasites on warm-blooded animals, characterised in that they contain, in addition to a compound of formula I, at least one further active ingredient having the same or different sphere of activity and at least one physiologically acceptable carrier. The present invention is not restricted to two-fold combinations.

As a rule, the anthelminthic compositions according to the invention contain 0.1 to 99% by weight, especially 0.1 to 95% by weight of active ingredient of formula I, Ia or mixtures thereof, 99.9 to 1% by weight, especially 99.8 to 5% by weight of a solid or liquid admixture, including 0 to 25% by weight, especially 0.1 to 25% by weight of a surfactant.

Application of the compositions according to the invention to the animals to be treated may take place topically, perorally, parenterally or subcutaneously, the composition being present in the form of solutions, emulsions, suspensions, (drenches), powders, tablets, boli, capsules and pour-on formulations.

The pour-on or spot-on method consists in applying the compound of formula I to a specific location of the skin or coat, advantageously to the neck or backbone of the animal. This takes place e.g. by applying a swab or spray of the pour-on or spot-on formulation to a relatively small area of the coat, from where the active substance is dispersed almost automatically over wide areas of the fur owing to the spreading nature of the components in the formulation and assisted by the animal's movements.

Pour-on or spot-on formulations suitably contain carriers, which promote rapid dispersement over the skin surface or in the coat of the host animal, and are generally regarded as spreading oils. Suitable carriers are e.g. oily solutions; alcoholic and isopropanolic solutions such as solutions of 2-octyldodecanol or oleyl alcohol; solutions in esters of monocarboxylic acids, such as isopropyl myristate, isopropyl palmitate, lauric acid oxalate, oleic acid oleyl ester, oleic acid decyl ester, hexyl laurate, oleyl oleate, decyl oleate, capric acid esters of saturated fat alcohols of chain length C₁₂-C₁₈; solutions of esters of dicarboxylic acids, such as dibutyl phthalate, diisopropyl isophthalate, adipic acid diisopropyl ester, di-n-butyl adipate or also solutions of esters of aliphatic acids, e.g. glycols. It may be advantageous for a dispersing agent to be additionally present, such as one known from the pharmaceutical or cosmetic industry. Examples are 2-pyrrolidone, 2-(N-alkyl)pyrrolidone, acetone, polyethylene glycol and the ethers and esters thereof, propylene glycol or synthetic triglycerides.

The oily solutions include e.g. vegetable oils such as olive oil, groundnut oil, sesame oil, pine oil, linseed oil or castor oil. The vegetable oils may also be present in epoxidised form. Paraffins and silicone oils may also be used.

A pour-on or spot-on formulation generally contains 1 to 20% by weight of a compound of formula I, 0.1 to 50% by weight of dispersing agent and 45 to 98.9% by weight of solvent.

The pour-on or spot-on method is especially advantageous for use on herd animals such as cattle, horses, sheep or pigs, in which it is difficult or time-consuming to treat all the animals orally or by injection. Because of its simplicity, this method can of course also be used for all other animals, including individual domestic animals or pets, and is greatly favoured by the keepers of the animals, as it can often be carried out without the specialist presence of the veterinarian.

Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.

Such compositions may also contain further additives, such as stabilisers, anti-foaming agents, viscosity regulators, binding agents or tackifiers, as well as other active ingredients, in order to achieve special effects.

Anthelminthic compositions of this type, which are used by the end user, similarly form a constituent of the present invention.

In each of the processes according to the invention for pest control of in each of the pest control compositions according to the invention, the active ingredients of formula I can be used in all of their steric configurations or in mixtures thereof.

The invention also includes a method of prophylactically protecting warm-blooded animals, especially productive livestock, domestic animals and pets, against parasitic helminths, which is characterised in that the active ingredients of the formula or the active ingredient formulations prepared therefrom are administered to the animals as an additive to the feed, or to the drinks or also in solid or liquid form, orally or by injection or parenterally. The invention also includes the compounds of formula I according to the invention for usage in one of the said processes.

The following examples serve merely to illustrate the invention without restricting it, the term active ingredient representing a substance listed in tables . . .

In particular, preferred formulations are made up as follows:

-   (%=percent by weight)

FORMULATION EXAMPLES

1. Granulate a) b) active ingredient 5% 10% kaolin 94%  — highly dispersed silicic acid 1% — attapulgite — 90%

The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent subsequently concentrated by evaporation under vacuum. Granulates of this kind can be mixed with the animal feed.

2. Granulate active ingredient 3% polyethylene glycol (mw 200) 3% kaolin 94%  (mw = molecular weight)

The finely ground active ingredient is evenly applied in a mixer to the kaolin which has been moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

3. Tablets or Boli

I active ingredient 33.00% methylcellulose 0.80% silicic acid, highly dispersed 0.80% corn starch 8.40% II lactose, cryst. 22.50% corn starch 17.00% microcryst. cellulose 16.50% magnesium stearate 1.00%

-   I Methyl cellulose is stirred into water. After the material has     swollen, silicic acid is stirred in and the mixture homogeneously     suspended. The active ingredient and the corn starch are mixed. The     aqueous suspension is worked into this mixture and kneaded to a     dough. The resulting mass is granulated through a 12 M sieve and     dried. -   II All 4 excipients are mixed thoroughly. -   III The preliminary mixes obtained according to I and II are mixed     and pressed into tablets or boli.     4. Injectables

A. Oily vehicle (slow release) 1. active ingredient 0.1–1.0 g  groundnut oil ad 100 ml 2. active ingredient 0.1–1.0 g  sesame oil ad 100 ml

Preparation: The active ingredient is dissolved in part of the oil whilst stirring and, if required, with gentle heating, then after cooling made up to the desired volume and sterile-filtered through a suitable membrane filter with a pore size of 0.22 μm.

B. Water-miscible solvent (average rate of release) active ingredient 0.1–1.0 g 4-hydroxymethyl-1,3-dioxolane (glycerol formal) 40 g 1,2-propanediol ad 100 ml active ingredient 0.1–1.0 g glycerol dimethyl ketal 40 g 1,2-propanediol ad 100 ml

Preparation: The active ingredient is dissolved in part of the solvent whilst stirring, made up to the desired volume and sterile-filtered through a suitable membrane filter with a pore size of 0.22 μm.

C. Aqueous solubilisate (rapid release) 1. active ingredient 0.1–1.0 g  polyethoxylated castor oil (40 ethylene oxide units) 10 g  1,2-propanediol 20 g  benzyl alcohol 1 g  aqua ad inject. ad 100 ml 2. active ingredient 0.1–1.0 g  polyethoxylated sorbitan monooleate 8 g  (20 ethylene oxide units)  4-hydroxymethyl-1,3-dioxolane (glycerol formal) 20 g  benzyl alcohol 1 g  aqua ad inject. ad 100 ml

Preparation: The active ingredient is dissolved in the solvents and the surfactant, and made up with water to the desired volume. Sterile filtration through an appropriate membrane filter of 0.22 μm pore size.

5. Pour on

A. active ingredient 5 g isopropyl myristate 10 g isopropanol ad 100 ml B active ingredient 2 g hexyl laurate 5 g medium-chained triglyceride 15 g ethanol ad 100 ml C. active ingredient 2 g oleyl oleate 5 g N-methyl-pyrrolidone 40 g isopropanol ad 100 ml

The aqueous systems may also preferably be used for oral and/or intraruminal application.

The compositions may also contain further additives, such as stabilisers, e.g. where appropriate epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil, or soybean oil); antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers, as well as fertilisers or other active ingredients to achieve special effects.

Further biologically active substances or additives, which are neutral towards the compounds of formula I and do not have a harmful effect on the host animal to be treated, as well as mineral salts or vitamins, may also be added to the described compositions. The following examples serve to illustrate the invention. They do not limit the invention. The letter ‘h’ stands for hour.

PREPARATION EXAMPLES Example 1 N-[1-cyano-1-methyl-2-(5-nitroindazol-1-yl)-ethyl]-4-trifluoromethoxybenzamide

-   a) 5 g of 5-nitroindazole, 3.97 g of chloroacetone, 1.84 g of     potassium carbonate and 0.46 g of potassium iodide are dissolved in     30 ml of acetone and boiled under reflux over night. After cooling,     the precipitate is filtered, concentrated by evaporation and the     residue purified by flash chromatography.     1-(5-nitroindazol-1-yl)-propan-2-one is thus obtained. -   b) 3.5 g of 1-(5-nitroindazol-1-yl)-propan-2-one, 0.94 g of sodium     cyanide and 1.28 g of ammonium chloride are suspended in 50 ml of     aqueous 25% ammonia solution and stirred at room temperature for     90 h. The crude product is subsequently extracted from the reaction     mixture with ethyl acetate, the organic phase is washed with     saturated sodium chloride solution, dried with magnesium sulphate     and concentrated by evaporation.     2-amino-2-methyl-3-(5-nitroindazol-1-yl)-propionitrile is thus     obtained. -   c) A mixture of 369 mg of ethyl diisopropylamine, 30 mg of     4-dimethylaminopyridine and 549 mg of 4-(trifluoromethoxy)-benzoyl     chloride is added dropwise to a solution of 500 mg of     2-amino-2-methyl-3-(5-nitroindazol-1-yl)-propionitrile in 8 ml of     methylene chloride, and subsequently stirred for 18 h at room     temperature. Subsequently, the reaction mixture is diluted with     ethyl acetate, then washed with a saturated sodium bicarbonate     solution, water, aqueous 2N hydrochloric acid and finally with     saturated sodium chloride solution. After drying the organic phase     with magnesium sulphate and concentrating by evaporation, the     residue is recrystallised in diethylether. In this way, the title     compound is obtained as a slightly yellowish solid with a melting     point of 203-5° C.

The substances named in the following table may also be prepared analogously to the above-described method. The values of the melting points are indicated in ° C. Bd. signifies a direct bond.

TABLE 1

No. Y₁ R₁ R₂ R₇₁ phys. data 1.1 Bd. H H H 1.2 Bd. H H 2-Cl 1.3 Bd. H H 3-Cl 1.4 Bd. H H 4-Cl 1.5 Bd. H H 2-F 1.6 Bd. H H 3-F 1.7 Bd. H H 4-F 1.8 Bd. H H 2-CH₃ 1.9 Bd. H H 3-CH₃ 1.10 Bd. H H 4-CH₃ 1.11 Bd. H H 2-OCH₃ 1.12 Bd. H H 3-OCH₃ 1.13 Bd. H H 4-OCH₃ 1.14 Bd. H H 2-CF₃ 1.15 Bd. H H 3-CF₃ 1.16 Bd. H H 4-CF₃ 1.17 Bd. H H 2-OCF₃ 1.18 Bd. H H 3-OCF₃ 1.19 Bd. H H 4-OCF₃ 1.20 Bd. H H 2-OCF₂CF₂ 1.21 Bd. H H 3-OCF₂CF₂ 1.22 Bd. H H 4-OCF₂CF₂ 1.23 Bd. H H 2-OC₂F₅ 1.24 Bd. H H 3-OC₂F₅ 1.25 Bd. H H 4-OC₂F₅ 1.26 Bd. H H 2-OC₆H₅ 1.27 Bd. H H 3-OC₆H₅ 1.28 Bd. H H 4-OC₆H₅ 1.29 Bd. H H 2-C(O)C₆H₅ 1.30 Bd. H H 3-C(O)C₆H₅ 1.31 Bd. H H 4-C(O)C₆H₅ 1.32 Bd. H H 4-CN 1.33 Bd. H CH₃ H 1.34 Bd. H CH₃ 2-Cl 1.35 Bd. H CH₃ 3-Cl 1.36 Bd. H CH₃ 4-Cl 1.37 Bd. H CH₃ 2-F 1.38 Bd. H CH₃ 3-F 1.39 Bd. H CH₃ 4-F 1.40 Bd. H CH₃ 2-CH₃ 1.41 Bd. H CH₃ 3-CH₃ 1.42 Bd. H CH₃ 4-CH₃ 1.43 Bd. H CH₃ 2-OCH₃ 1.44 Bd. H CH₃ 3-OCH₃ 1.45 Bd. H CH₃ 4-OCH₃ 1.46 Bd. H CH₃ 2-CF₃ 1.47 Bd. H CH₃ 3-CF₃ 1.48 Bd. H CH₃ 4-CF₃ 1.49 Bd. H CH₃ 2-OCF₃ 1.50 Bd. H CH₃ 3-OCF₃ 1.51 Bd. H CH₃ 4-OCF₃ 1.52 Bd. H CH₃ 2-OCF₂CF₂ 1.53 Bd. H CH₃ 3-OCF₂CF₂ 1.54 Bd. H CH₃ 4-OCF₂CF₂ 1.55 Bd. H CH₃ 2-OC₂F₅ 1.56 Bd. H CH₃ 3-OC₂F₅ 1.57 Bd. H CH₃ 4-OC₂F₅ 1.58 Bd. H CH₃ 2-OC₆H₅ 1.59 Bd. H CH₃ 3-OC₆H₅ 1.60 Bd. H CH₃ 4-OC₆H₅ 1.61 Bd. H CH₃ 2-C(O)C₆H₅ 1.62 Bd. H CH₃ 3-C(O)C₆H₅ 1.63 Bd. H CH₃ 4-C(O)C₆H₅ 1.64 Bd. H CH₃ 4-CN 1.65 Bd. H CF₃ H 1.66 Bd. H CF₃ 2-Cl 1.67 Bd. H CF₃ 3-Cl 1.68 Bd. H CF₃ 4-Cl 1.69 Bd. H CF₃ 2-F 1.70 Bd. H CF₃ 3-F 1.71 Bd. H CF₃ 4-F 1.72 Bd. H CF₃ 2-CH₃ 1.73 Bd. H CF₃ 3-CH₃ 1.74 Bd. H CF₃ 4-CH₃ 1.75 Bd. H CF₃ 2-OCH₃ 1.76 Bd. H CF₃ 3-OCH₃ 1.77 Bd. H CF₃ 4-OCH₃ 1.78 Bd. H CF₃ 2-CF₃ 1.79 Bd. H CF₃ 3-CF₃ 1.80 Bd. H CF₃ 4-CF₃ 1.81 Bd. H CF₃ 2-OCF₃ 1.82 Bd. H CF₃ 3-OCF₃ 1.83 Bd. H CF₃ 4-OCF₃ 1.84 Bd. H CF₃ 2-OCF₂CF₂ 1.85 Bd. H CF₃ 3-OCF₂CF₂ 1.86 Bd. H CF₃ 4-OCF₂CF₂ 1.87 Bd. H CF₃ 2-OC₂F₅ 1.88 Bd. H CF₃ 3-OC₂F₅ 1.89 Bd. H CF₃ 4-OC₂F₅ 1.90 Bd. H CF₃ 2-OC₆H₅ 1.91 Bd. H CF₃ 3-OC₆H₅ 1.92 Bd. H CF₃ 4-OC₆H₅ 1.93 Bd. H CF₃ 2-C(O)C₆H₅ 1.94 Bd. H CF₃ 3-C(O)C₆H₅ 1.95 Bd. H CF₃ 4-C(O)C₆H₅ 1.96 Bd. H CF₃ 4-CN 1.97 Bd. 4-OCH₃ H H 1.98 Bd. 4-OCH₃ H 2-Cl 1.99 Bd. 4-OCH₃ H 3-Cl 1.100 Bd. 4-OCH₃ H 4-Cl 1.101 Bd. 4-OCH₃ H 2-F 1.102 Bd. 4-OCH₃ H 3-F 1.103 Bd. 4-OCH₃ H 4-F 1.104 Bd. 4-OCH₃ H 2-CH₃ 1.105 Bd. 4-OCH₃ H 3-CH₃ 1.106 Bd. 4-OCH₃ H 4-CH₃ 1.107 Bd. 4-OCH₃ H 2-OCH₃ 1.108 Bd. 4-OCH₃ H 3-OCH₃ 1.109 Bd. 4-OCH₃ H 4-OCH₃ 1.110 Bd. 4-OCH₃ H 2-CF₃ 1.111 Bd. 4-OCH₃ H 3-CF₃ 1.112 Bd. 4-OCH₃ H 4-CF₃ 1.113 Bd. 4-OCH₃ H 2-OCF₃ 1.114 Bd. 4-OCH₃ H 3-OCF₃ 1.115 Bd. 4-OCH₃ H 4-OCF₃ 1.116 Bd. 4-OCH₃ H 2-OCF₂CF₂ 1.117 Bd. 4-OCH₃ H 3-OCF₂CF₂ 1.118 Bd. 4-OCH₃ H 4-OCF₂CF₂ 1.119 Bd. 4-OCH₃ H 2-OC₂F₅ 1.120 Bd. 4-OCH₃ H 3-OC₂F₅ 1.121 Bd. 4-OCH₃ H 4-OC₂F₅ 1.122 Bd. 4-OCH₃ H 2-OC₆H₅ 1.123 Bd. 4-OCH₃ H 3-OC₆H₅ 1.124 Bd. 4-OCH₃ H 4-OC₆H₅ 1.125 Bd. 4-OCH₃ H 2-C(O)C₆H₅ 1.126 Bd. 4-OCH₃ H 3-C(O)C₆H₅ 1.127 Bd. 4-OCH₃ H 4-C(O)CeH₅ 1.128 Bd. 4-OCH₃ H 4-CN 1.129 Bd. 4-OCH₃ CH₃ H 1.130 Bd. 4-OCH₃ CH₃ 2-Cl 1.131 Bd. 4-OCH₃ CH₃ 3-Cl 1.132 Bd. 4-OCH₃ CH₃ 4-Cl 1.133 Bd. 4-OCH₃ CH₃ 2-F 1.134 Bd. 4-OCH₃ CH₃ 3-F 1.135 Bd. 4-OCH₃ CH₃ 4-F 1.136 Bd. 4-OCH₃ CH₃ 2-CH₃ 1.137 Bd. 4-OCH₃ CH₃ 3-CH₃ 1.138 Bd. 4-OCH₃ CH₃ 4-CH₃ 1.139 Bd. 4-OCH₃ CH₃ 2-OCH₃ 1.140 Bd. 4-OCH₃ CH₃ 3-OCH₃ 1.141 Bd. 4-OCH₃ CH₃ 4-OCH₃ 1.142 Bd. 4-OCH₃ CH₃ 2-CF₃ 1.143 Bd. 4-OCH₃ CH₃ 3-CF₃ 1.144 Bd. 4-OCH₃ CH₃ 4-CF₃ 1.145 Bd. 4-OCH₃ CH₃ 2-OCF₃ 1.146 Bd. 4-OCH₃ CH₃ 3-OCF₃ 1.147 Bd. 4-OCH₃ CH₃ 4-OCF₃ 1.148 Bd. 4-OCH₃ CH₃ 2-OCF₂CF₂ 1.149 Bd. 4-OCH₃ CH₃ 3-OCF₂CF₂ 1.150 Bd. 4-OCH₃ CH₃ 4-OCF₂CF₂ 1.151 Bd. 4-OCH₃ CH₃ 2-OC₂F₅ 1.152 Bd. 4-OCH₃ CH₃ 3-OC₂F₅ 1.153 Bd. 4-OCH₃ CH₃ 4-OC₂F₅ 1.154 Bd. 4-OCH₃ CH₃ 2-OC₆H₅ 1.155 Bd. 4-OCH₃ CH₃ 3-OC₆H₅ 1.156 Bd. 4-OCH₃ CH₃ 4-OC₆H₅ 1.157 Bd. 4-OCH₃ CH₃ 2-C(O)C₆H₅ 1.158 Bd. 4-OCH₃ CH₃ 3-C(O)C₆H₅ 1.159 Bd. 4-OCH₃ CH₃ 4-C(O)C₆H₅ 1.160 Bd. 4-OCH₃ CH₃ 4-CN 1.161 Bd. 4-OCH₃ CF₃ H 1.162 Bd. 4-OCH₃ CF₃ 2-Cl 1.163 Bd. 4-OCH₃ CF₃ 3-Cl 1.164 Bd. 4-OCH₃ CF₃ 4-Cl 1.165 Bd. 4-OCH₃ CF₃ 2-F 1.166 Bd. 4-OCH₃ CF₃ 3-F 1.167 Bd. 4-OCH₃ CF₃ 4-F 1.168 Bd. 4-OCH₃ CF₃ 2-CH₃ 1.169 Bd. 4-OCH₃ CF₃ 3-CH₃ 1.170 Bd. 4-OCH₃ CF₃ 4-CH₃ 1.171 Bd. 4-OCH₃ CF₃ 2-OCH₃ 1.172 Bd. 4-OCH₃ CF₃ 3-OCH₃ 1.173 Bd. 4-OCH₃ CF₃ 4-OCH₃ 1.174 Bd. 4-OCH₃ CF₃ 2-CF₃ 1.175 Bd. 4-OCH₃ CF₃ 3-CF₃ 1.176 Bd. 4-OCH₃ CF₃ 4-CF₃ 1.177 Bd. 4-OCH₃ CF₃ 2-OCF₃ 1.178 Bd. 4-OCH₃ CF₃ 3-OCF₃ 1.179 Bd. 4-OCH₃ CF₃ 4-OCF₃ 1.180 Bd. 4-OCH₃ CF₃ 2-OCF₂CF₂ 1.181 Bd. 4-OCH₃ CF₃ 3-OCF₂CF₂ 1.182 Bd. 4-OCH₃ CF₃ 4-OCF₂CF₂ 1.183 Bd. 4-OCH₃ CF₃ 2-OC₂F₅ 1.184 Bd. 4-OCH₃ CF₃ 3-OC₂F₅ 1.185 Bd. 4-OCH₃ CF₃ 4-OC₂F₅ 1.186 Bd. 4-OCH₃ CF₃ 2-OC₆H₅ 1.187 Bd. 4-OCH₃ CF₃ 3-OC₆H₅ 1.188 Bd. 4-OCH₃ CF₃ 4-OC₆H₅ 1.189 Bd. 4-OCH₃ CF₃ 2-C(O)C₆H₅ 1.190 Bd. 4-OCH₃ CF₃ 3-C(O)C₆H₅ 1.191 Bd. 4-OCH₃ CF₃ 4-C(O)C₆H₅ 1.192 Bd. 4-OCH₃ CF₃ 4-CN 1.193 Bd. 5-Cl H H 1.194 Bd. 5-Cl H 2-Cl 1.195 Bd. 5-Cl H 3-Cl 1.196 Bd. 5-Cl H 4-Cl 1.197 Bd. 5-Cl H 2-F 1.198 Bd. 5-Cl H 3-F 1.199 Bd. 5-Cl H 4-F 1.200 Bd. 5-Cl H 2-CH₃ 1.201 Bd. 5-Cl H 3-CH₃ 1.202 Bd. 5-Cl H 4-CH₃ 1.203 Bd. 5-Cl H 2-OCH₃ 1.204 Bd. 5-Cl H 3-OCH₃ 1.205 Bd. 5-Cl H 4-OCH₃ 1.206 Bd. 5-Cl H 2-CF₃ 1.207 Bd. 5-Cl H 3-CF₃ 1.208 Bd. 5-Cl H 4-CF₃ 1.209 Bd. 5-Cl H 2-OCF₃ 1.210 Bd. 5-Cl H 3-OCF₃ 1.211 Bd. 5-Cl H 4-OCF₃ m.p. 1.75–6° 1.212 Bd. 5-Cl H 2-OCF₂CF₂ 1.213 Bd. 5-Cl H 3-OCF₂CF₂ 1.214 Bd. 5-Cl H 4-OCF₂CF₂ 1.215 Bd. 5-Cl H 2-OC₂F₅ 1.216 Bd. 5-Cl H 3-OC₂F₅ 1.217 Bd. 5-Cl H 4-OC₂F₅ 1.218 Bd. 5-Cl H 2-OC₆H₅ 1.219 Bd. 5-Cl H 3-OC₆H₅ 1.220 Bd. 5-Cl H 4-OC₆H₅ 1.221 Bd. 5-Cl H 2-C(O)C₆H₅ 1.222 Bd. 5-Cl H 3-C(O)C₆H₅ 1.223 Bd. 5-Cl H 4-C(O)C₆H₅ 1.224 Bd. 5-Cl H 4-CN 1.225 Bd. 5-Cl CH₃ H 1.226 Bd. 5-Cl CH₃ 2-Cl 1.227 Bd. 5-Cl CH₃ 3-Cl 1.228 Bd. 5-Cl CH₃ 4-Cl 1.229 Bd. 5-Cl CH₃ 2-F 1.230 Bd. 5-Cl CH₃ 3-F 1.231 Bd. 5-Cl CH₃ 4-F 1.232 Bd. 5-Cl CH₃ 2-CH₃ 1.233 Bd. 5-Cl CH₃ 3-CH₃ 1.234 Bd. 5-Cl CH₃ 4-CH₃ 1.235 Bd. 5-Cl CH₃ 2-OCH₃ 1.236 Bd. 5-Cl CH₃ 3-OCH₃ 1.237 Bd. 5-Cl CH₃ 4-OCH₃ 1.238 Bd. 5-Cl CH₃ 2-CF₃ 1.239 Bd. 5-Cl CH₃ 3-CF₃ 1.240 Bd. 5-Cl CH₃ 4-CF₃ 1.241 Bd. 5-Cl CH₃ 2-OCF₃ 1.242 Bd. 5-Cl CH₃ 3-OCF₃ 1.243 Bd. 5-Cl CH₃ 4-OCF₃ 1.244 Bd. 5-Cl CH₃ 2-OCF₂CF₂ 1.245 Bd. 5-Cl CH₃ 3-OCF₂CF₂ 1.246 Bd. 5-Cl CH₃ 4-OCF₂CF₂ 1.247 Bd. 5-Cl CH₃ 2-OC₂F₅ 1.248 Bd. 5-Cl CH₃ 3-OC₂F₅ 1.249 Bd. 5-Cl CH₃ 4-OC₂F₅ 1.250 Bd. 5-Cl CH₃ 2-OC₆H₅ 1.251 Bd. 5-Cl CH₃ 3-OC₂H₅ 1.252 Bd. 5-Cl CH₃ 4-OC₆H₅ 1.253 Bd. 5-Cl CH₃ 2-C(O)C₆H₅ 1.254 Bd. 5-Cl CH₃ 3-C(O)C₆H₅ 1.255 Bd. 5-Cl CH₃ 4-C(O)C₆H₅ 1.256 Bd. 5-Cl CH₃ 4-CN 1.257 Bd. 5-Cl CF₃ H 1.258 Bd. 5-Cl CF₃ 2-Cl 1.259 Bd. 5-Cl CF₃ 3-Cl 1.260 Bd. 5-Cl CF₃ 4-Cl 1.261 Bd. 5-Cl CF₃ 2-F 1.262 Bd. 5-Cl CF₃ 3-F 1.263 Bd. 5-Cl CF₃ 4-F 1.264 Bd. 5-Cl CF₃ 2-CH₃ 1.265 Bd. 5-Cl CF₃ 3-CH₃ 1.266 Bd. 5-Cl CF₃ 4-CH₃ 1.267 Bd. 5-Cl CF₃ 2-OCH₃ 1.268 Bd. 5-Cl CF₃ 3-OCH₃ 1.269 Bd. 5-Cl CF₃ 4-OCH₃ 1.270 Bd. 5-Cl CF₃ 2-CF₃ 1.271 Bd. 5-Cl CF₃ 3-CF₃ 1.272 Bd. 5-Cl CF₃ 4-CF₃ 1.273 Bd. 5-Cl CF₃ 2-OCF₃ 1.274 Bd. 5-Cl CF₃ 3-OCF₃ 1.275 Bd. 5-Cl CF₃ 4-OCF₃ 1.276 Bd. 5-Cl CF₃ 2-OCF₂CF₂ 1.277 Bd. 5-Cl CF₃ 3-OCF₂CF₂ 1.278 Bd. 5-Cl CF₃ 4-OCF₂CF₂ 1.279 Bd. 5-Cl CF₃ 2-OC₂F₅ 1.280 Bd. 5-Cl CF₃ 3-OC₂F₅ 1.281 Bd. 5-Cl CF₃ 4-OC₂F₅ 1.282 Bd. 5-Cl CF₃ 2-OC₆H₅ 1.283 Bd. 5-Cl CF₃ 3-OC₆H₅ 1.284 Bd. 5-Cl CF₃ 4-OC₆H₅ 1.285 Bd. 5-Cl CF₃ 2-C(O)C₆H₅ 1.286 Bd. 5-Cl CF₃ 3-C(O)C₆H₅ 1.287 Bd. 5-Cl CF₃ 4-C(O)C₆H₅ 1.288 Bd. 5-Cl CF₃ 4-CN 1.289 Bd. 5-NO₂ H H 1.290 Bd. 5-NO₂ H 2-Cl 1.291 Bd. 5-NO₂ H 3-Cl 1.292 Bd. 5-NO₂ H 4-Cl 1.293 Bd. 5-NO₂ H 2-F 1.294 Bd. 5-NO₂ H 3-F 1.295 Bd. 5-NO₂ H 4-F 1.296 Bd. 5-NO₂ H 2-CH₃ 1.297 Bd. 5-NO₂ H 3-CH₃ 1.298 Bd. 5-NO₂ H 4-CH₃ 1.299 Bd. 5-NO₂ H 2-OCH₃ 1.300 Bd. 5-NO₂ H 3-OCH₃ 1.301 Bd. 5-NO₂ H 4-OCH₃ 1.302 Bd. 5-NO₂ H 2-CF₃ 1.303 Bd. 5-NO₂ H 3-CF₃ 1.304 Bd. 5-NO₂ H 4-CF₃ m.p. 195° 1.305 Bd. 5-NO₂ H 2-OCF₃ 1.306 Bd. 5-NO₂ H 3-OCF₃ 1.307 Bd. 5-NO₂ H 4-OCF₃ m.p. 203–5° 1.308 Bd. 5-NO₂ H 2-OCF₂CF₂ 1.309 Bd. 5-NO₂ H 3-OCF₂CF₂ 1.310 Bd. 5-NO₂ H 4-OCF₂CF₂ 1.311 Bd. 5-NO₂ H 2-OC₂F₅ 1.312 Bd. 5-NO₂ H 3-OC₂F₅ 1.313 Bd. 5-NO₂ H 4-OC₂F₅ 1.314 Bd. 5-NO₂ H 2-OC₆H₅ 1.315 Bd. 5-NO₂ H 3-OC₆H₅ 1.316 Bd. 5-NO₂ H 4-OC₆H₅ m.p. 189° 1.317 Bd. 5-NO₂ H 2-C(O)C₆H₅ 1.318 Bd. 5-NO₂ H 3-C(O)C₆H₅ 1.319 Bd. 5-NO₂ H 4-C(O)C₆H₅ m.p. 154° 1.320 Bd. 5-NO₂ H 4-CN m.p. 260° 1.321 Bd. 5-NO₂ CH₃ H 1.322 Bd. 5-NO₂ CH₃ 2-Cl 1.323 Bd. 5-NO₂ CH₃ 3-Cl 1.324 Bd. 5-NO₂ CH₃ 4-Cl 1.325 Bd. 5-NO₂ CH₃ 2-F 1.326 Bd. 5-NO₂ CH₃ 3-F 1.327 Bd. 5-NO₂ CH₃ 4-F 1.328 Bd. 5-NO₂ CH₃ 2-CH₃ 1.329 Bd. 5-NO₂ CH₃ 3-CH₃ 1.330 Bd. 5-NO₂ CH₃ 4-CH₃ 1.331 Bd. 5-NO₂ CH₃ 2-OCH₃ 1.332 Bd. 5-NO₂ CH₃ 3-OCH₃ 1.333 Bd. 5-NO₂ CH₃ 4-OCH₃ 1.334 Bd. 5-NO₂ CH₃ 2-CF₃ 1.335 Bd. 5-NO₂ CH₃ 3-CF₃ 1.336 Bd. 5-NO₂ CH₃ 4-CF₃ 1.337 Bd. 5-NO₂ CH₃ 2-OCF₃ 1.338 Bd. 5-NO₂ CH₃ 3-OCF₃ 1.339 Bd. 5-NO₂ CH₃ 4-OCF₃ 1.340 Bd. 5-NO₂ CH₃ 2-OCF₂CF₂ 1.341 Bd. 5-NO₂ CH₃ 3-OCF₂CF₂ 1.342 Bd. 5-NO₂ CH₃ 4-OCF₂CF₂ 1.343 Bd. 5-NO₂ CH₃ 2-OC₂F₅ 1.344 Bd. 5-NO₂ CH₃ 3-OC₂F₅ 1.345 Bd. 5-NO₂ CH₃ 4-OC₂F₅ 1.346 Bd. 5-NO₂ CH₃ 2-OC₆H₅ 1.347 Bd. 5-NO₂ CH₃ 3-OC₆H₅ 1.348 Bd. 5-NO₂ CH₃ 4-OC₆H₅ 1.349 Bd. 5-NO₂ CH₃ 2-C(O)C₆H₅ 1.350 Bd. 5-NO₂ CH₃ 3-C(O)C₆H₅ 1.351 Bd. 5-NO₂ CH₃ 4-C(O)C₆H₅ 1.352 Bd. 5-NO₂ CH₃ 4-CN 1.353 Bd. 5-NO₂ CF₃ H 1.354 Bd. 5-NO₂ CF₃ 2-Cl 1.355 Bd. 5-NO₂ CF₃ 3-Cl 1.356 Bd. 5-NO₂ CF₃ 4-Cl 1.357 Bd. 5-NO₂ CF₃ 2-F 1.358 Bd. 5-NO₂ CF₃ 3-F 1.359 Bd. 5-NO₂ CF₃ 4-F 1.360 Bd. 5-NO₂ CF₃ 2-CH₃ 1.361 Bd. 5-NO₂ CF₃ 3-CH₃ 1.362 Bd. 5-NO₂ CF₃ 4-CH₃ 1.363 Bd. 5-NO₂ CF₃ 2-OCH₃ 1.364 Bd. 5-NO₂ CF₃ 3-OCH₃ 1.365 Bd. 5-NO₂ CF₃ 4-OCH₃ 1.366 Bd. 5-NO₂ CF₃ 2-CF₃ 1.367 Bd. 5-NO₂ CF₃ 3-CF₃ 1.368 Bd. 5-NO₂ CF₃ 4-CF₃ 1.369 Bd. 5-NO₂ CF₃ 2-OCF₃ 1.370 Bd. 5-NO₂ CF₃ 3-OCF₃ 1.371 Bd. 5-NO₂ CF₃ 4-OCF₃ 1.372 Bd. 5-NO₂ CF₃ 2-OCF₂CF₂ 1.373 Bd. 5-NO₂ CF₃ 3-OCF₂CF₂ 1.374 Bd. 5-NO₂ CF₃ 4-OCF₂CF₂ 1.375 Bd. 5-NO₂ CF₃ 2-OC₂F₅ 1.376 Bd. 5-NO₂ CF₃ 3-OC₂F₅ 1.377 Bd. 5-NO₂ CF₃ 4-OC₂F₅ 1.378 Bd. 5-NO₂ CF₃ 2-OC₆H₅ 1.379 Bd. 5-NO₂ CF₃ 3-OC₆H₅ 1.380 Bd. 5-NO₂ CF₃ 4-OC₆H₅ 1.381 Bd. 5-NO₂ CF₃ 2-C(O)C₆H₅ 1.382 Bd. 5-NO₂ CF₃ 3-C(O)C₆H₅ 1.383 Bd. 5-NO₂ CF₃ 4-C(O)C₆H₅ 1.384 Bd. 5-NO₂ CF₃ 4-CN 1.385 CH₂O H H H 1.386 CH₂O H H 2-Cl 1.387 CH₂O H H 3-Cl 1.388 CH₂O H H 4-Cl 1.389 CH₂O H H 2-F 1.390 CH₂O H H 3-F 1.391 CH₂O H H 4-F 1.392 CH₂O H H 2-CH₃ 1.393 CH₂O H H 3-CH₃ 1.394 CH₂O H H 4-CH₃ 1.395 CH₂O H H 2-OCH₃ 1.396 CH₂O H H 3-OCH₃ 1.397 CH₂O H H 4-OCH₃ 1.398 CH₂O H H 2-CF₃ 1.399 CH₂O H H 3-CF₃ 1.400 CH₂O H H 4-CF₃ 1.401 CH₂O H H 2-OCF₃ 1.402 CH₂O H H 3-OCF₃ 1.403 CH₂O H H 4-OCF₃ 1.404 CH₂O H H 2-OCF₂CF₂ 1.405 CH₂O H H 3-OCF₂CF₂ 1.406 CH₂O H H 4-OCF₂CF₂ 1.407 CH₂O H H 2-OC₂F₅ 1.408 CH₂O H H 3-OC₂F₅ 1.409 CH₂O H H 4-OC₂F₅ 1.410 CH₂O H H 2-OC₆H₅ 1.411 CH₂O H H 3-OC₆H₅ 1.412 CH₂O H H 4-OC₆H₅ 1.413 CH₂O H H 2-C(O)C₆H₅ 1.414 CH₂O H H 3-C(O)C₆H₅ 1.415 CH₂O H H 4-C(O)C₆H₅ 1.416 CH₂O H H 4-CN 1.417 CH₂O H CH₃ H 1.418 CH₂O H CH₃ 2-Cl 1.419 CH₂O H CH₃ 3-Cl 1.420 CH₂O H CH₃ 4-Cl 1.421 CH₂O H CH₃ 2-F 1.422 CH₂O H CH₃ 3-F 1.423 CH₂O H CH₃ 4-F 1.424 CH₂O H CH₃ 2-CH₃ 1.425 CH₂O H CH₃ 3-CH₃ 1.426 CH₂O H CH₃ 4-CH₃ 1.427 CH₂O H CH₃ 2-OCH₃ 1.428 CH₂O H CH₃ 3-OCH₃ 1.429 CH₂O H CH₃ 4-OCH₃ 1.430 CH₂O H CH₃ 2-CF₃ 1.431 CH₂O H CH₃ 3-CF₃ 1.432 CH₂O H CH₃ 4-CF₃ 1.433 CH₂O H CH₃ 2-OCF₃ 1.434 CH₂O H CH₃ 3-OCF₃ 1.435 CH₂O H CH₃ 4-OCF₃ 1.436 CH₂O H CH₃ 2-OCF₂CF₂ 1.437 CH₂O H CH₃ 3-OCF₂CF₂ 1.438 CH₂O H CH₃ 4-OCF₂CF₂ 1.439 CH₂O H CH₃ 2-OC₂F₅ 1.440 CH₂O H CH₃ 3-OC₂F₅ 1.441 CH₂O H CH₃ 4-OC₂F₅ 1.442 CH₂O H CH₃ 2-OC₆H₅ 1.443 CH₂O H CH₃ 3-OC₆H₅ 1.444 CH₂O H CH₃ 4-OC₆H₅ 1.445 CH₂O H CH₃ 2-C(O)C₆H₅ 1.446 CH₂O H CH₃ 3-C(O)C₆H₅ 1.447 CH₂O H CH₃ 4-C(O)C₆H₅ 1.448 CH₂O H CH₃ 4-CN 1.449 CH₂O H CF₃ H 1.450 CH₂O H CF₃ 2-Cl 1.451 CH₂O H CF₃ 3-Cl 1.452 CH₂O H CF₃ 4-Cl 1.453 CH₂O H CF₃ 2-F 1.454 CH₂O H CF₃ 3-F 1.455 CH₂O H CF₃ 4-F 1.456 CH₂O H CF₃ 2-CH₃ 1.457 CH₂O H CF₃ 3-CH₃ 1.458 CH₂O H CF₃ 4-CH₃ 1.459 CH₂O H CF₃ 2-OCH₃ 1.460 CH₂O H CF₃ 3-OCH₃ 1.461 CH₂O H CF₃ 4-OCH₃ 1.462 CH₂O H CF₃ 2-CF₃ 1.463 CH₂O H CF₃ 3-CF₃ 1.464 CH₂O H CF₃ 4-CF₃ 1.465 CH₂O H CF₃ 2-OCF₃ 1.466 CH₂O H CF₃ 3-OCF₃ 1.467 CH₂O H CF₃ 4-OCF₃ 1.468 CH₂O H CF₃ 2-OCF₂CF₂ 1.469 CH₂O H CF₃ 3-OCF₂CF₂ 1.470 CH₂O H CF₃ 4-OCF₂CF₂ 1.471 CH₂O H CF₃ 2-OC₂F₅ 1.472 CH₂O H CF₃ 3-OC₂F₅ 1.473 CH₂O H CF₃ 4-OC₂F₅ 1.474 CH₂O H CF₃ 2-OC₆H₅ 1.475 CH₂O H CF₃ 3-OC₆H₅ 1.476 CH₂O H CF₃ 4-OC₆H₅ 1.477 CH₂O H CF₃ 2-C(O)C₆H₅ 1.478 CH₂O H CF₃ 3-C(O)C₆H₅ 1.479 CH₂O H CF₃ 4-C(O)C₆H₅ 1.480 CH₂O H CF₃ 4-CN 1.481 CH₂O 4-OCH₃ H H 1.482 CH₂O 4-OCH₃ H 2-Cl 1.483 CH₂O 4-OCH₃ H 3-Cl 1.484 CH₂O 4-OCH₃ H 4-Cl 1.485 CH₂O 4-OCH₃ H 2-F 1.486 CH₂O 4-OCH₃ H 3-F 1.487 CH₂O 4-OCH₃ H 4-F 1.488 CH₂O 4-OCH₃ H 2-CH₃ 1.489 CH₂O 4-OCH₃ H 3-CH₃ 1.490 CH₂O 4-OCH₃ H 4-CH₃ 1.491 CH₂O 4-OCH₃ H 2-OCH₃ 1.492 CH₂O 4-OCH₃ H 3-OCH₃ 1.493 CH₂O 4-OCH₃ H 4-OCH₃ 1.494 CH₂O 4-OCH₃ H 2-CF₃ 1.495 CH₂O 4-OCH₃ H 3-CF₃ 1.496 CH₂O 4-OCH₃ H 4-CF₃ 1.497 CH₂O 4-OCH₃ H 2-OCF₃ 1.498 CH₂O 4-OCH₃ H 3-OCF₃ 1.499 CH₂O 4-OCH₃ H 4-OCF₃ 1.500 CH₂O 4-OCH₃ H 2-OCF₂CF₂ 1.501 CH₂O 4-OCH₃ H 3-OCF₂CF₂ 1.502 CH₂O 4-OCH₃ H 4-OCF₂CF₂ 1.503 CH₂O 4-OCH₃ H 2-OC₂F₅ 1.504 CH₂O 4-OCH₃ H 3-OC₂F₅ 1.505 CH₂O 4-OCH₃ H 4-OC₂F₅ 1.506 CH₂O 4-OCH₃ H 2-OC₆H₅ 1.507 CH₂O 4-OCH₃ H 3-OC₆H₅ 1.508 CH₂O 4-OCH₃ H 4-OC₆H₅ 1.509 CH₂O 4-OCH₃ H 2-C(O)C₆H₅ 1.510 CH₂O 4-OCH₃ H 3-C(O)C₆H₅ 1.511 CH₂O 4-OCH₃ H 4-C(O)C₆H₅ 1.512 CH₂O 4-OCH₃ H 4-CN 1.513 CH₂O 4-OCH₃ CH₃ H 1.514 CH₂O 4-OCH₃ CH₃ 2-Cl 1.515 CH₂O 4-OCH₃ CH₃ 3-Cl 1.516 CH₂O 4-OCH₃ CH₃ 4-Cl 1.517 CH₂O 4-OCH₃ CH₃ 2-F 1.518 CH₂O 4-OCH₃ CH₃ 3-F 1.519 CH₂O 4-OCH₃ CH₃ 4-F 1.520 CH₂O 4-OCH₃ CH₃ 2-CH₃ 1.521 CH₂O 4-OCH₃ CH₃ 3-CH₃ 1.522 CH₂O 4-OCH₃ CH₃ 4-CH₃ 1.523 CH₂O 4-OCH₃ CH₃ 2-OCH₃ 1.524 CH₂O 4-OCH₃ CH₃ 3-OCH₃ 1.525 CH₂O 4-OCH₃ CH₃ 4-OCH₃ 1.526 CH₂O 4-OCH₃ CH₃ 2-CF₃ 1.527 CH₂O 4-OCH₃ CH₃ 3-CF₃ 1.528 CH₂O 4-OCH₃ CH₃ 4-CF₃ 1.529 CH₂O 4-OCH₃ CH₃ 2-OCF₃ 1.530 CH₂O 4-OCH₃ CH₃ 3-OCF₃ 1.531 CH₂O 4-OCH₃ CH₃ 4-OCF₃ 1.532 CH₂O 4-OCH₃ CH₃ 2-OCF₂CF₂ 1.533 CH₂O 4-OCH₃ CH₃ 3-OCF₂CF₂ 1.534 CH₂O 4-OCH₃ CH₃ 4-OCF₂CF₂ 1.535 CH₂O 4-OCH₃ CH₃ 2-OC₂F₅ 1.536 CH₂O 4-OCH₃ CH₃ 3-OC₂F₅ 1.537 CH₂O 4-OCH₃ CH₃ 4-OC₂F₅ 1.538 CH₂O 4-OCH₃ CH₃ 2-OC₆H₅ 1.539 CH₂O 4-OCH₃ CH₃ 3-OC₆H₅ 1.540 CH₂O 4-OCH₃ CH₃ 4-OC₆H₅ 1.541 CH₂O 4-OCH₃ CH₃ 2-C(O)C₆H₅ 1.542 CH₂O 4-OCH₃ CH₃ 3-C(O)C₆H₅ 1.543 CH₂O 4-OCH₃ CH₃ 4-C(O)C₆H₅ 1.544 CH₂O 4-OCH₃ CH₃ 4-CN 1.545 CH₂O 4-OCH₃ CF₃ H 1.546 CH₂O 4-OCH₃ CF₃ 2-Cl 1.547 CH₂O 4-OCH₃ CF₃ 3-Cl 1.548 CH₂O 4-OCH₃ CF₃ 4-Cl 1.549 CH₂O 4-OCH₃ CF₃ 2-F 1.550 CH₂O 4-OCH₃ CF₃ 3-F 1.551 CH₂O 4-OCH₃ CF₃ 4-F 1.552 CH₂O 4-OCH₃ CF₃ 2-CH₃ 1.553 CH₂O 4-OCH₃ CF₃ 3-CH₃ 1.554 CH₂O 4-OCH₃ CF₃ 4-CH₃ 1.555 CH₂O 4-OCH₃ CF₃ 2-OCH₃ 1.556 CH₂O 4-OCH₃ CF₃ 3-OCH₃ 1.557 CH₂O 4-OCH₃ CF₃ 4-OCH₃ 1.558 CH₂O 4-OCH₃ CF₃ 2-CF₃ 1.559 CH₂O 4-OCH₃ CF₃ 3-CF₃ 1.560 CH₂O 4-OCH₃ CF₃ 4-CF₃ 1.561 CH₂O 4-OCH₃ CF₃ 2-OCF₃ 1.562 CH₂O 4-OCH₃ CF₃ 3-OCF₃ 1.563 CH₂O 4-OCH₃ CF₃ 4-OCF₃ 1.564 CH₂O 4-OCH₃ CF₃ 2-OCF₂CF₂ 1.565 CH₂O 4-OCH₃ CF₃ 3-OCF₂CF₂ 1.566 CH₂O 4-OCH₃ CF₃ 4-OCF₂CF₂ 1.567 CH₂O 4-OCH₃ CF₃ 2-OC₂F₅ 1.568 CH₂O 4-OCH₃ CF₃ 3-OC₂F₅ 1.569 CH₂O 4-OCH₃ CF₃ 4-OC₂F₅ 1.570 CH₂O 4-OCH₃ CF₃ 2-OC₆H₅ 1.571 CH₂O 4-OCH₃ CF₃ 3-OC₆H₅ 1.572 CH₂O 4-OCH₃ CF₃ 4-OC₆H₅ 1.573 CH₂O 4-OCH₃ CF₃ 2-C(O)C₆H₅ 1.574 CH₂O 4-OCH₃ CF₃ 3-C(O)C₆H₅ 1.575 CH₂O 4-OCH₃ CF₃ 4-C(O)C₆H₅ 1.576 CH₂O 4-OCH₃ CF₃ 4-CN 1.577 CH₂O 5-Cl H H 1.578 CH₂O 5-Cl H 2-Cl 1.579 CH₂O 5-Cl H 3-Cl 1.580 CH₂O 5-Cl H 4-Cl 1.581 CH₂O 5-Cl H 2-F 1.582 CH₂O 5-Cl H 3-F 1.583 CH₂O 5-Cl H 4-F 1.584 CH₂O 5-Cl H 2-CH₃ 1.585 CH₂O 5-Cl H 3-CH₃ 1.586 CH₂O 5-Cl H 4-CH₃ 1.587 CH₂O 5-Cl H 2-OCH₃ 1.588 CH₂O 5-Cl H 3-OCH₃ 1.589 CH₂O 5-Cl H 4-OCH₃ 1.590 CH₂O 5-Cl H 2-CF₃ 1.591 CH₂O 5-Cl H 3-CF₃ 1.592 CH₂O 5-Cl H 4-CF₃ 1.593 CH₂O 5-Cl H 2-OCF₃ 1.594 CH₂O 5-Cl H 3-OCF₃ 1.595 CH₂O 5-Cl H 4-OCF₃ 1.596 CH₂O 5-Cl H 2-OCF₂CF₂ 1.597 CH₂O 5-Cl H 3-OCF₂CF₂ 1.598 CH₂O 5-Cl H 4-OCF₂CF₂ 1.599 CH₂O 5-Cl H 2-OC₂F₅ 1.600 CH₂O 5-Cl H 3-OC₂F₅ 1.601 CH₂O 5-Cl H 4-OC₂F₅ 1.602 CH₂O 5-Cl H 2-OC₆H₅ 1.603 CH₂O 5-Cl H 3-OC₆H₅ 1.604 CH₂O 5-Cl H 4-OC₆H₅ 1.605 CH₂O 5-Cl H 2-C(O)C₆H₅ 1.606 CH₂O 5-Cl H 3-C(O)C₆H₅ 1.607 CH₂O 5-Cl H 4-C(O)C₆H₅ 1.608 CH₂O 5-Cl H 4-CN 1.609 CH₂O 5-Cl CH₃ H 1.610 CH₂O 5-Cl CH₃ 2-Cl 1.611 CH₂O 5-Cl CH₃ 3-Cl 1.612 CH₂O 5-Cl CH₃ 4-Cl 1.613 CH₂O 5-Cl CH₃ 2-F 1.614 CH₂O 5-Cl CH₃ 3-F 1.615 CH₂O 5-Cl CH₃ 4-F 1.616 CH₂O 5-Cl CH₃ 2-CH₃ 1.617 CH₂O 5-Cl CH₃ 3-CH₃ 1.618 CH₂O 5-Cl CH₃ 4-CH₃ 1.619 CH₂O 5-Cl CH₃ 2-OCH₃ 1.620 CH₂O 5-Cl CH₃ 3-OCH₃ 1.621 CH₂O 5-Cl CH₃ 4-OCH₃ 1.622 CH₂O 5-Cl CH₃ 2-CF₃ 1.623 CH₂O 5-Cl CH₃ 3-CF₃ 1.624 CH₂O 5-Cl CH₃ 4-CF₃ 1.625 CH₂O 5-Cl CH₃ 2-OCF₃ 1.626 CH₂O 5-Cl CH₃ 3-OCF₃ 1.627 CH₂O 5-Cl CH₃ 4-OCF₃ 1.628 CH₂O 5-Cl CH₃ 2-OCF₂CF₂ 1.629 CH₂O 5-Cl CH₃ 3-OCF₂CF₂ 1.630 CH₂O 5-Cl CH₃ 4-OCF₂CF₂ 1.631 CH₂O 5-Cl CH₃ 2-OC₂F₅ 1.632 CH₂O 5-Cl CH₃ 3-OC₂F₅ 1.633 CH₂O 5-Cl CH₃ 4-OC₂F₅ 1.634 CH₂O 5-Cl CH₃ 2-OC₆H₅ 1.635 CH₂O 5-Cl CH₃ 3-OC₆H₅ 1.636 CH₂O 5-Cl CH₃ 4-OC₆H₅ 1.637 CH₂O 5-Cl CH₃ 2-C(O)C₆H₅ 1.638 CH₂O 5-Cl CH₃ 3-C(O)C₆H₅ 1.639 CH₂O 5-Cl CH₃ 4-C(O)C₆H₅ 1.640 CH₂O 5-Cl CH₃ 4-CN 1.641 CH₂O 5-Cl CF₃ H 1.642 CH₂O 5-Cl CF₃ 2-Cl 1.643 CH₂O 5-Cl CF₃ 3-Cl 1.644 CH₂O 5-Cl CF₃ 4-Cl 1.645 CH₂O 5-Cl CF₃ 2-F 1.646 CH₂O 5-Cl CF₃ 3-F 1.647 CH₂O 5-Cl CF₃ 4-F 1.648 CH₂O 5-Cl CF₃ 2-CH₃ 1.649 CH₂O 5-Cl CF₃ 3-CH₃ 1.650 CH₂O 5-Cl CF₃ 4-CH₃ 1.651 CH₂O 5-Cl CF₃ 2-OCH₃ 1.652 CH₂O 5-Cl CF₃ 3-OCH₃ 1.653 CH₂O 5-Cl CF₃ 4-OCH₃ 1.654 CH₂O 5-Cl CF₃ 2-CF₃ 1.655 CH₂O 5-Cl CF₃ 3-CF₃ 1.656 CH₂O 5-Cl CF₃ 4-CF₃ 1.657 CH₂O 5-Cl CF₃ 2-OCF₃ 1.658 CH₂O 5-Cl CF₃ 3-OCF₃ 1.659 CH₂O 5-Cl CF₃ 4-OCF₃ 1.660 CH₂O 5-Cl CF₃ 2-OCF₂CF₂ 1.661 CH₂O 5-Cl CF₃ 3-OCF₂CF₂ 1.662 CH₂O 5-Cl CF₃ 4-OCF₂CF₂ 1.663 CH₂O 5-Cl CF₃ 2-OC₂F₅ 1.664 CH₂O 5-Cl CF₃ 3-OC₂F₅ 1.665 CH₂O 5-Cl CF₃ 4-OC₂F₅ 1.666 CH₂O 5-Cl CF₃ 2-OC₆H₅ 1.667 CH₂O 5-Cl CF₃ 3-OC₆H₅ 1.668 CH₂O 5-Cl CF₃ 4-OC₆H₅ 1.669 CH₂O 5-Cl CF₃ 2-C(O)C₆H₅ 1.670 CH₂O 5-Cl CF₃ 3-C(O)C₆H₅ 1.671 CH₂O 5-Cl CF₃ 4-C(O)CeH₅ 1.672 CH₂O 5-Cl CF₃ 4-CN 1.673 CH₂O 5-NO₂ H H 1.674 CH₂O 5-NO₂ H 2-Cl m.p. 92° 1.675 CH₂O 5-NO₂ H 3-Cl 1.676 CH₂O 5-NO₂ H 4-Cl 1.677 CH₂O 5-NO₂ H 2-F 1.678 CH₂O 5-NO₂ H 3-F 1.679 CH₂O 5-NO₂ H 4-F 1.680 CH₂O 5-NO₂ H 2-CH₃ 1.681 CH₂O 5-NO₂ H 3-CH₃ 1.682 CH₂O 5-NO₂ H 4-CH₃ 1.683 CH₂O 5-NO₂ H 2-OCH₃ 1.684 CH₂O 5-NO₂ H 3-OCH₃ 1.685 CH₂O 5-NO₂ H 4-OCH₃ 1.686 CH₂O 5-NO₂ H 2-CF₃ 1.687 CH₂O 5-NO₂ H 3-CF₃ 1.688 CH₂O 5-NO₂ H 4-CF₃ 1.689 CH₂O 5-NO₂ H 2-OCF₃ 1.690 CH₂O 5-NO₂ H 3-OCF₃ 1.691 CH₂O 5-NO₂ H 4-OCF₃ 1.692 CH₂O 5-NO₂ H 2-OCF₂CF₂ 1.693 CH₂O 5-NO₂ H 3-OCF₂CF₂ 1.694 CH₂O 5-NO₂ H 4-OCF₂CF₂ 1.695 CH₂O 5-NO₂ H 2-OC₂F₅ 1.696 CH₂O 5-NO₂ H 3-OC₂F₅ 1.697 CH₂O 5-NO₂ H 4-OC₂F₅ 1.698 CH₂O 5-NO₂ H 2-OC₆H₅ 1.699 CH₂O 5-NO₂ H 3-OC₆H₅ 1.700 CH₂O 5-NO₂ H 4-OC₆H₅ 1.701 CH₂O 5-NO₂ H 2-C(O)C₆H₅ 1.702 CH₂O 5-NO₂ H 3-C(O)C₆H₅ 1.703 CH₂O 5-NO₂ H 4-C(O)C₆H₅ 1.704 CH₂O 5-NO₂ H 4-CN 1.705 CH₂O 5-NO₂ CH₃ H 1.706 CH₂O 5-NO₂ CH₃ 2-Cl 1.707 CH₂O 5-NO₂ CH₃ 3-Cl 1.708 CH₂O 5-NO₂ CH₃ 4-Cl 1.709 CH₂O 5-NO₂ CH₃ 2-F 1.710 CH₂O 5-NO₂ CH₃ 3-F 1.711 CH₂O 5-NO₂ CH₃ 4-F 1.712 CH₂O 5-NO₂ CH₃ 2-CH₃ 1.713 CH₂O 5-NO₂ CH₃ 3-CH₃ 1.714 CH₂O 5-NO₂ CH₃ 4-CH₃ 1.715 CH₂O 5-NO₂ CH₃ 2-OCH₃ 1.716 CH₂O 5-NO₂ CH₃ 3-OCH₃ 1.717 CH₂O 5-NO₂ CH₃ 4-OCH₃ 1.718 CH₂O 5-NO₂ CH₃ 2-CF₃ 1.719 CH₂O 5-NO₂ CH₃ 3-CF₃ 1.720 CH₂O 5-NO₂ CH₃ 4-CF₃ 1.721 CH₂O 5-NO₂ CH₃ 2-OCF₃ 1.722 CH₂O 5-NO₂ CH₃ 3-OCF₃ 1.723 CH₂O 5-NO₂ CH₃ 4-OCF₃ 1.724 CH₂O 5-NO₂ CH₃ 2-OCF₂CF₂ 1.725 CH₂O 5-NO₂ CH₃ 3-OCF₂CF₂ 1.726 CH₂O 5-NO₂ CH₃ 4-OCF₂CF₂ 1.727 CH₂O 5-NO₂ CH₃ 2-OC₂F₅ 1.728 CH₂O 5-NO₂ CH₃ 3-OC₂F₅ 1.729 CH₂O 5-NO₂ CH₃ 4-OC₂F₅ 1.730 CH₂O 5-NO₂ CH₃ 2-OC₆H₅ 1.731 CH₂O 5-NO₂ CH₃ 3-OC₆H₅ 1.732 CH₂O 5-NO₂ CH₃ 4-OC₆H₅ 1.733 CH₂O 5-NO₂ CH₃ 2-C(O)C₆H₅ 1.734 CH₂O 5-NO₂ CH₃ 3-C(O)C₆H₅ 1.735 CH₂O 5-NO₂ CH₃ 4-C(O)C₆H₅ 1.736 CH₂O 5-NO₂ CH₃ 4-CN 1.737 CH₂O 5-NO₂ CF₃ H 1.738 CH₂O 5-NO₂ CF₃ 2-Cl 1.739 CH₂O 5-NO₂ CF₃ 3-Cl 1.740 CH₂O 5-NO₂ CF₃ 4-Cl 1.741 CH₂O 5-NO₂ CF₃ 2-F 1.742 CH₂O 5-NO₂ CF₃ 3-F 1.743 CH₂O 5-NO₂ CF₃ 4-F 1.744 CH₂O 5-NO₂ CF₃ 2-CH₃ 1.745 CH₂O 5-NO₂ CF₃ 3-CH₃ 1.746 CH₂O 5-NO₂ CF₃ 4-CH₃ 1.747 CH₂O 5-NO₂ CF₃ 2-OCH₃ 1.748 CH₂O 5-NO₂ CF₃ 3-OCH₃ 1.749 CH₂O 5-NO₂ CF₃ 4-OCH₃ 1.750 CH₂O 5-NO₂ CF₃ 2-CF₃ 1.751 CH₂O 5-NO₂ CF₃ 3-CF₃ 1.752 CH₂O 5-NO₂ CF₃ 4-CF₃ 1.753 CH₂O 5-NO₂ CF₃ 2-OCF₃ 1.754 CH₂O 5-NO₂ CF₃ 3-OCF₃ 1.755 CH₂O 5-NO₂ CF₃ 4-OCF₃ 1.756 CH₂O 5-NO₂ CF₃ 2-OCF₂CF₂ 1.757 CH₂O 5-NO₂ CF₃ 3-OCF₂CF₂ 1.758 CH₂O 5-NO₂ CF₃ 4-OCF₂CF₂ 1.759 CH₂O 5-NO₂ CF₃ 2-OC₂F₅ 1.760 CH₂O 5-NO₂ CF₃ 3-OC₂F₅ 1.761 CH₂O 5-NO₂ CF₃ 4-OC₂F₅ 1.762 CH₂O 5-NO₂ CF₃ 2-OC₆H₅ 1.763 CH₂O 5-NO₂ CF₃ 3-OC₆H₅ 1.764 CH₂O 5-NO₂ CF₃ 4-OC₆H₅ 1.765 CH₂O 5-NO₂ CF₃ 2-C(O)C₆H₅ 1.766 CH₂O 5-NO₂ CF₃ 3-C(O)C₆H₅ 1.767 CH₂O 5-NO₂ CF₃ 4-C(O)C₆H₅ 1.768 CH₂O 5-NO₂ CF₃ 4-CN

BIOLOGICAL EXAMPLES

1. In-Vivo Test on Trichostrongylus colubriformis and Haemonchus contortus on Mongolian Gerbils (Meriones unguiculatus) Using Peroral Application

Six to eight week old Mongolian gerbils are infected by artificial feeding with ca. 2000 third instar larvae each of T. colubriformis and H. contortus. 6 days after infection, the gerbils are lightly anaesthetised with N₂O and treated by peroral application with the test compounds, dissolved in a mixture of 2 parts DMSO and 1 part polyethylene glycol (PEG 300), in quantities of 100, 32 and 10-0.1 mg/kg. On day 9 (3 days after treatment), when most of the H. contortus that are still present are late 4th instar larvae and most of the T. colubriformis are immature adults, the gerbils are killed in order to count the worms. The efficacy is calculated as the % reduction of the number of worms in each gerbil, compared with the geometric average of number of worms from 8 infected and untreated gerbils.

In this test, a vast reduction in nematode infestation is achieved with compounds of formula I, especially from Table 1.

To examine the insecticidal and/or acaricidal activity of the compounds of formula I on animals and plants, the following test methods may be used.

2. Activity on L₁ Larvae of Lucilia sericata

1 ml of an aqueous suspension of the active substance to be tested is admixed with 3 ml of a special larvae growth medium at ca. 50° C., so that a homogenate of either 250 or 125 ppm of active ingredient content is obtained. Ca. 30 Lucilia larvae (L₁) are used in each test tube sample. After 4 days, the mortality rate is determined.

3. Acaricidal Activity on Boophilus Microplus (Biarra Strain)

A piece of sticky tape is attached horizontally to a PVC sheet, so that 10 fully engorged female ticks of Boophilus microplus (Biarra strain) can be adhered thereto by their backs, side by side, in a row. Using an injection needle, 1 μl of a liquid is injected into each tick. The liquid is a 1:1 mixture of polyethylene glycol and acetone and it contains, dissolved therein, a certain amount of active ingredient chosen from 1, 0.1 or 0.01 μg per tick. Control animals are given an injection without active ingredient. After treatment, the animals are kept under normal conditions in an insectarium at ca. 28° C. and at 80% relative humidity until oviposition takes place and the larvae have hatched from the eggs of the control animals. The activity of a tested substance is determined by IR₉₀, i.e. an evaluation is made of the dosage of active ingredient at which 9 out of 10 female ticks (=90%) lay eggs that are infertile even after 30 days.

4. In Vitro Efficacy on Engorged Female Boophilus Microplus (BIARRA)

4×10 engorged female ticks of the OP-resistant BIARRA strain are adhered to a sticky strip and covered for 1 hour with a cotton-wool ball soaked in an emulsion or suspension of the test compound in concentrations of 500, 125, 31 and 8 ppm respectively. Evaluation takes place 28 days later based on mortality, oviposition and hatched larvae.

An indication of the activity of the test compounds is shown by the number of females that

-   -   die quickly before laying eggs,     -   survive for some time without laying eggs,     -   lay eggs in which no embryos are formed,     -   lay eggs in which embryos form, from which no larvae hatch, and     -   lay eggs in which embryos form, from which larvae normally hatch         within 26 to 27 days.         5. In Vitro Efficacy on Nymphs of Amblyomma hebraeum

About 5 fasting nymphs are placed in a polystyrene test tube containing 2 ml of the test compound in solution, suspension or emulsion.

After immersion for 10 minutes, and shaking for 2×10 seconds on a vortex mixer, the test tubes are blocked up with a tight wad of cotton wool and rotated. As soon as all the liquid has been soaked up by the cotton wool ball, it is pushed half-way into the test tube which is still being rotated, so that most of the liquid is squeezed out of the cotton-wool ball and flows into a Petri dish below.

The test tubes are then kept at room temperature in a room with daylight until evaluated. After 14 days, the test tubes are immersed in a beaker of boiling water. If the ticks begin to move in reaction to the heat, the test substance is inactive at the tested concentration, otherwise the ticks are regarded as dead and the test substances regarded as active at the tested concentration. All substances are tested in a concentration range of 0.1 to 100 ppm.

6. Activity Against Dermanyssus gallinae

2 to 3 ml of a solution containing 10 ppm active ingredient, and ca. 200 mites (Dermanyssus gallinae) at different stages of development are added to a glass container which is open at the top. Then the container is closed with a wad of cotton wool, shaken for 10 minutes until the mites are completely wet, and then inverted briefly so that the remaining test solution can be absorbed by the cotton wool. After 3 days, the mortality of the mites is determined by counting the dead individuals and indicated as a percentage.

7. Activity Against Musca domestica

A sugar cube is treated with a solution of the test substance in such a way that the concentration of test substance in the sugar, after drying over night, is 250 ppm. The cube treated in this way is placed on an aluminium dish with wet cotton wool and 10 adult Musca domestica of an OP-resistant strain, covered with a beaker and incubated at 25° C. The mortality rate is determined after 24 hours. 

1. A compound of formula (I)

wherein R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkylthio, C₁-C₆-alkoxy, C₃-C₆-cycloalkyloxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino or unsubstituted or substituted phenoxy, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; R₂ signifies hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkylthio, C₁-C₆-alkoxy, C₃-C₆-cycloalkyloxy, halo-C₁-C₆-alkoxy, C₁-₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, NR₈R₉, hetaryl which is unsubstituted or substituted once or many times, phenyl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy and halo-C₁-C₆-alkoxy; R₃, R₄ and R₅ either, independently of one another, signify hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl; C₃-C₆-cycloalkyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen and C₁-C₆-alkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino or di-(C₁-C₆-alkyl)amino; or R₄ and R₅ together signify C₂-C₆-alkylene; R₆ signifies hydrogen, C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, aminocarbonyl, C₁-C₆-alkoxycarbonyl, halo-C₁-C₆-alkylcarbonyl, thio-C₁-C₆-alkylcarbonyl or benzyl; R₇ signifies hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloatkyloxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyloxy, halo-C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylsulfonylamino, halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, di(C₁-C₆-alkyl)aminocarbonyl; aryl-C₁-C₆-alkyl which is unsubstituted or substituted once or many times, arylamino which is unsubstituted or substituted once or many times, arylcarbonyl which is unsubstituted or substituted once or many times, arylcarbonyloxy which is unsubstituted or substituted once or many times, aryloxy which is unsubstituted or substituted once or many times, aryloxy-C₁-C₆-alkyl which is unsubstituted or substituted once or many times, hetaryloxy-C₁-C₆-alkyl which is unsubstituted or substituted once or many times, aryloxycarbonyl which is unsubstituted or substituted once or many times, arylsulfonyl which is unsubstituted or substituted once or many times, arylsulfonylamino which is unsubstituted or substituted once or many times, pyridyloxy which is unsubstituted or substituted once or many times, and phenylacetylenyl which is unsubstituted or substituted once or many times, whereby the substituents may each be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; hetaryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and di(C₁-C₆-alkyl)amino; or unsubstituted naphthyl or quinolyl, or naphthyl or quinolyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; R₈ and R₉, independently of one another, signify hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylthiocarbonyl, thio-C₁-C₆-alkylcarbonyl, aryl or hetaryl; Y signifies a direct bond, C(O), C(S) or S(O)_(n); a signifies 1, 2 or 3; and n is 1 or 2, whereby said compound is in free form or salt form.
 2. A compound of formula (I), according to claim 1, wherein R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl or unsubstituted or substituted phenoxy, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy.
 3. A compound of formula (I), according to claim 1, wherein R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, or unsubstituted or substituted phenoxy, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy.
 4. A compound of formula (I), according to claim 1, wherein R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy or halo-C₁-C₂-alkoxy.
 5. A compound of formula (I), according to claim 1, wherein R₂ signifies hydrogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkylthio, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy or C₁-C₄-alkylsulfonyl.
 6. A compound of formula (I), according to claim 1, wherein R₂ signifies hydrogen, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy or halo-C₁-C₂-alkoxy.
 7. A compound of formula (I), according to claim 1, wherein R₂ is hydrogen, methyl or halomethyl.
 8. A compound of formula (I), according to claim 1, wherein R₃, R₄ and R₅, independently of one another, are hydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy; C₁-C₄-alkylthio and halo-C₁-C₄-alkylthio; or R₄ and R₅ together are C₂-C₆-alkylene.
 9. A compound of formula (I) according to claim 1, wherein R_(3,) R₄ and R₅ are hydrogen, halogen, C₁-C₂-alkyl, halo-C₁-C₂-alkyl or C₃-C₆-cycloalkyl.
 10. A compound of formula (I) according to claim 1, wherein R_(3,) R₄ and R₅ are hydrogen, methyl or halomethyl.
 11. A compound of formula (I), according to claim 1, wherein R₆ is hydrogen, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl or benzyl.
 12. A compound of formula (I), according to claim 1, wherein R₆ is hydrogen, C₁-C₂-alkyl, C₁-C₂-alkylcarbonyl or benzyl.
 13. A compound of formula (I) according to claim 1, wherein R₆ is hydrogen or C₁-C₂-alkyl.
 14. A compound of formula (I), according to claim 1, wherein R₇ signifies aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkinyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyloxy, halo-C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylsulfonyl, halo-C₁-C₄-alkylsulfonyl, C₂-C₄-alkenylsulfonyl, halo-C₂-C₄-alkenylsulfonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxycarbonyl; aryl-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, aryloxy which is unsubstituted or substituted once or many times, aryloxy-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, hetaryloxy-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, aryloxycarbonyl which is unsubstituted or substituted once or many times, arylsulfonyl which is unsubstituted or substituted once or many times, and pyridyloxy which is unsubstituted or substituted once or many times, whereby the substituents may each be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁₋₄-alkylthio, halo-C₁₋₄-alkylthio, C₁-C₄-alkylsulfonyl and halo-C₁-C₄-alkylsulfonyl; hetaryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl and halo-C₁-C₄-alkylsulfonyl; or naphthyl or quinolyl which are unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₂-C₄-alkenylthio, halo-C₂-C₄-alkenylthio, C₁-C₄-alkylsulfonyl and halo-C₁-C₄-alkylsulfonyl.
 15. A compound of formula (I), according to claim 1, wherein R₇ signifies aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₃-C₅-cycloalkyl, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl, halo-C₁-C₂-alkylsulfonyl, C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl; aryl-C₁-C₂-alkyl which is unsubstituted or substituted once or many times, aryloxy which is unsubstituted or substituted once or many times, aryloxy-C₁-C₂-alkyl which is unsubstituted or substituted once or many times, and pyridyloxy which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl and halo-C₁-C₂-alkylsulfonyl; or hetaryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl and halo-C₁-C₂-alkylsulfonyl.
 16. A compound of formula (I), according to claim 1, wherein R₇ signifies aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₃-C₅-cycloalkyl, C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl; aryl-C₁-C₂-alkyl which is unsubstituted or substituted once or many times, and aryloxy-C_(1.)C₂-alkyl which is unsubstituted or substituted once or many times, whereby the substituents may each be independent of one another and are selected from the group consisting of halogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy and halo-C₁-C₂-alkoxy.
 17. A compound of formula (I), according to claim 1, wherein R₈ and R₉ independently of one another, are hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl or aryl.
 18. A compound of formula (I) according to claim 1, wherein R₈ and R₉ independently of one another are hydrogen or C₁-C₄-alkyl.
 19. A compound of formula (I) according to claim 1, wherein R₈ and R₉ independently of one another are hydrogen or C₁-C₂-alkyl.
 20. A compound of formula (I), according to claim 1, wherein Y is C(O) or S(O)_(n).
 21. A compound of formula (I), according to claim 1, wherein Y is C(O).
 22. A compound of formula (I) according to claim 1, wherein a is 1 or
 2. 23. A compound of formula (I) according to claim 1, wherein a is
 1. 24. A compound of formula (I) according to claim 1, wherein n is
 2. 25. A compound of formula (I), according to claim 1, wherein R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl or unsubstituted or substituted phenoxy, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy; R₂ is hydrogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkylthio, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy or C₁-C₄-alkylsulfonyl; R₃, R₄ and R₅, independently of one another, are hydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy; C₁-C₄-alkylthio and halo-C₁-C₄-alkylthio; or R₄ and R₅ together are C₂-C₆-alkylene; R₆ is hydrogen, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl or benzyl; R₇ signifies aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkinyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyloxy, halo-C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylsulfonyl, halo-C₁-C₄-alkylsulfonyl, C₂-C₄-alkenylsulfonyl, halo-C₂-C₄-alkenylsulfonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxycarbonyl; aryl-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, aryloxy which is unsubstituted or substituted once or many times, aryloxy-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, hetaryloxy-C₁-C₄-alkyl which is unsubstituted or substituted once or many times, aryloxycarbonyl which is unsubstituted or substituted once or many times, arylsulfonyl which is unsubstituted or substituted once or many times, and pyridyloxy which is unsubstituted or substituted once or many times, whereby the substituents may each be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl and halo-C₁-C₄-alkylsulfonyl; hetaryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl and halo-C₁-C₄-alkylsulfonyl; or naphthyl or quinolyl which are unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₂-C₄-alkenylthio, halo-C₂-C₄-alkenylthio, C₁-C₄-alkylsulfonyl and halo-C₁-C₄-alkylsulfonyl; R₈ and R₉ independently of one another, signify hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl or aryl; Y is C(O) or S(O)_(n); a signifies 1 or 2;and n is
 2. 26. A compound of formula (I), according to claim 1, wherein R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, or unsubstituted or substituted phenoxy, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy; R₂ signifies hydrogen, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy or halo-C₁-C₂-alkoxy; R₃, R₄ and R₅, independently of one another, signify hydrogen, halogen, C₁-C₂-alkyl, halo-C₁-C₂-alkyl or C₃-C₆-cycloalkyl; R₆ signifies hydrogen, C₁-C₂-alkyl, C₁-C₂-alkylcarbonyl or benzyl; R₇ signifies aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₃-C₅-cycloalkyl, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl, halo-C₁-C₂-alkylsulfonyl, C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl; aryl-C₁-C₂-alkyl which is unsubstituted or substituted once or many times, aryloxy which is unsubstituted or substituted once or many times, aryloxy-C₁-C₂-alkyl which is unsubstituted or substituted once or many times, and pyridyloxy which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl and halo-C₁-C₂-alkylsulfonyl; or hetaryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylsulfonyl and halo-C₁-C₂-alkylsulfonyl; R₈ and R₉, independently of one another, signify hydrogen or C₁-C₄-alkyl; Y signifies C(O); a signifies 1; and n is
 2. 27. A compound of formula (I), according to claim 1, wherein R₁ signifies hydrogen, halogen, cyano, nitro, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy or halo-C₁-C₂-alkoxy; R₂ is hydrogen, methyl or halomethyl; R₃, R₄ and R₅, independently of one another, signify hydrogen, methyl or halomethyl; R₆ signifies hydrogen or C₁-C₂-alkyl; R₇ signifies aryl which is unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₃-C₅-cycloalkyl, C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl; aryl-C₁-C₂-alkyl which is unsubstituted or substituted once or many times, and aryloxy-C₁-C₂-alkyl which is unsubstituted or substituted once or many times, whereby the substituents may each be independent of one another and are selected from the group consisting of halogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy and halo-C₁-C₂-alkoxy; R₈ and R₉, independently of one another, signify hydrogen or C₁-C₂-alkyl; Y signifies C(O); a signifies 1; and n is
 2. 28. A compound of formula (I), according to claim 1, having the name N-[1-cyano-1-methyl-2-(5-nitroindazol-1-yl)-ethyl]-4-trifluoromethoxybenzamide.
 29. A method for the preparation of compounds of formula (I), respectively in free form or in salt form, according to claim 1, whereby a compound of formula (II)

which is known or may be produced analogously to corresponding known compounds, and wherein R₁, R₂, R₃, R₄, R₅, R₆ and a are defined as given for formula (I), is reacted with a compound of formula (III) Q—Y—R₇  III, which is known or may be prepared analogously to corresponding known compounds, and wherein Y and R₇ are defined as given for formula (I) and Q is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula (I) obtainable according to the method or in another way, respectively in free form or in salt form, is converted into another compound of formula (I), a mixture of isomers obtainable according to the method is separated and the desired isomer isolated and/or a free compound of formula (I) obtainable according to the method is converted into a salt or a salt of a compound of formula (I) obtainable according to the method is converted into the free compound of formula (I) or into another salt.
 30. A method for the preparation of compounds of formula (II), respectively in free form or in salt form, according to claim 29, whereby a compound of formula (IV)

which is known or may be produced analogously to corresponding known compounds, in which R₁, R₂, R₃, R₄, R₅ and a are defined as for formula (I), is reacted with an inorganic or organic cyanide and a compound of formula R₆-NH₂, which is known or may be produced analogously to corresponding known compounds and wherein R₆ is defined as for formula (I), and if desired, a compound of formula (II) obtainable according to the method or in another way, respectively in free form or in salt form, is converted into another compound of formula (II), a mixture of isomers obtainable according to the method is separated and the desired isomer isolated and/or a free compound of formula (II) obtainable according to the method is converted into a salt or a salt of a compound of formula (II) obtainable according to the method is converted into the free compound of formula (II) or into another salt.
 31. Composition for the control of parasites comprising at least one compound of formula (I) according to claim 1, in addition to carriers and/or dispersants.
 32. A method of treating an animal for parasites comprising administering to said animal in need of treatment thereof a parasiticidal effective amount of the composition of claim
 31. 33. The method of claim 32 wherein said administration to said animal is topically, perorally, parenterally, or subcutaneously.
 34. The method of claim 32 wherein said composition of claim 31 is in a formulation consisting of the group of pour-on, spot-on, tablet, chewie, powder, boli, capsules, suspension, emulsion, solution, injectable, water-additive, and food-additive.
 35. The method of claim 32 wherein said parasites are endoparasites.
 36. The method of claim 32 wherein said parasites are helminthes. 